Supporting Information for

Preparation of 3-diazoindolin-2-imines via cascade reaction

between indoles and sulfonylazides and their extensions to
2,3-diaminoindoles and imidazo[4,5-b]indoles

Guorong Sheng, Kai Huang, Zhihao Chi, Hualong Ding, Yanpeng Xing, Ping Lu*,
and Yanguang Wang*

1 
 
 CONTENTS

General Information S3

Table S1 Optimization of the reaction conditions S4

General Procedures S5

Analysis Data of Products S7

Copies of 1H & 13C NMR Spectra S31

Crystal Structures of 3d, 3l and 4g S97

2 
 
General Information
Melting points were recorded on a SGW X-4. NMR spectra were obtained on a
Bruker AVANCE DMX400 spectrometer operating at 400 MHz for 1H-NMR, 100
13
MHz for C-NMR. Unless otherwise noted, all the NMR spectra were recorded at
room temperature. Chemical shifts were quoted in parts per million (ppm) referenced
to the appropriate solvent peak or 0.0 ppm for tetramethylsilane. The following
abbreviations were used to describe peak splitting patterns when appropriate: s =
singlet, d = doublet, t = triplet, m = multiplet. Coupling constants (J values) were
reported in hertz unit (Hz). Chemical shifts (in ppm) were referenced to
13
tetramethylsilane (δ = 0 ppm) in CDCl3 and DMSO- d6 as an internal standard. C
NMR spectra were obtained by using the same NMR spectrometers and chemical
shifts were reported in ppm referenced to the center line of a triplet at 77.0 ppm of
CDCl3 or the center line of a heptet at 39.6 ppm of DMSO- d6. High resolution mass
spectra (HRMS) were recorded on Waters GCT Premier (EI) and Agilent
Technologies 6224 TOF LC/MS apparatus (ESI). IR spectra were run on a Bruker
vector 22 spectrometer. Flash column chromatography was performed employing
300-400 mesh silica gel. Thin layer chromatography (TLC) was performed on silica
gel HSGF254.
Substrates 1a-b and 1e-f were prepared according to the published procedures.[1] 1c
was prepared using the standard procedures.[2] 1d was prepared according to the
published procedures.[3] 2a-f were prepared using the standard procedures.[4]

References
[1] A. D. kong, X. L. Han, X. Y. Lu, Org. Lett. 2006, 8, 1339–1342

[2] P. Y. Choy, C. P. Lau, F. Y. Kwong, J. Org. Chem. 2011, 76 , 80–84.

[3]        X. H. Xu, G. K. Liu, A. Azuma, E. Tokunaga, N. Shibata, Org. Lett. 2011, 13, 4854–4857.

[4] Y. P. Xing, G. R. Sheng, J. Wang, P. Lu, and Y. G. Wang, Org. Lett. 2014, 16, 1244−1247.

3 
 
Table S1. Optimization of the reaction conditionsa

Entry Solvent Volume (mL) Temperature (oC) Time (h) Yield (%)b
1 DMSO 2 40 16 15
2 THF 2 40 16 Trace
3 CH3CN 2 40 16 6
4 PhCH3 2 40 16 4
5 DCM 2 40 16 10
6 DCE 2 40 16 5
7 DMF 2 40 16 6
8 DMSO 1.5 40 16 22
9 DMSO 1 40 16 36
10 DMSO 0.5 40 16 61
11 DMSO 0.25 40 16 59
12 DMSO 0.5 rt 16 37
13 DMSO 0.5 30 16 47
14 DMSO 0.5 50 16 70
15 DMSO 0.5 60 16 67
16 DMSO 0.5 70 16 49
17 DMSO 0.5 80 16 45
18 DMSO 0.5 50 24 61
19 DMSO 0.5 50 12 70
20 DMSO 0.5 50 8 49
21 DMSO 0.5 50 12 45c
22 DMSO 0.5 50 12 59d
23 DMSO 0.5 50 12 68e
24 DMSO 0.5 50 12 68f
25 DCM 0.5 50 12 50e
26 DMSO 0.5 50 12 0g
27 DCM 0.5 50 12 0h
a
Reaction conditions: 1a (0.25 mmol), 2a (0.5 mmol), solvent, air; b Isolated yield; c 1a (0.25
mmol) and 2a (0.25 mmol); d 1a (0.5 mmol) and 2a (0.25 mmol); e 1a (0.25 mmol) and 2a (0.75
mmol); f The reaction was performed under O2; g DDQ (0.5 mmol) was used; h The reaction was
performed under N2 and 4a was isolated in 7% yield with 90% recovery of 1a.

4 
 
General Procedures
1.Gen eral procedure for the preparation of compounds 3
To an oven-dried 10 mL Schlenk tube equipped with a magnetic stirring bar were
added sequentially indole 1 (0.25 mmol), sulfonyl azide 2 (0.5 mmol), and DMSO
(0.5 mL). The reaction mixture was stirred at 50 oC for 12 h. Then, the reaction was
quenched by H2O (10 mL) and extracted with CH2Cl2 (15 mL  3). The combined
organic layers were dried over anhydrous Na2SO4 and concentrated in vacuo. The
crude product was purified by column chromatography on silica gel (petroleum ether /
EtOAc = 3:1).

2. General procedure for the preparation of compounds 4c-i

To an oven-dried 10 mL Schlenk tube equipped with a magnetic stirring bar were
added sequentially indole 1b-d (0.25 mmol), sulfonyl azides 2 (0.5 mmol), and
DMSO (0.5 mL). The reaction mixture was stirred at 50 oC for 72 hours. The reaction
was quenched by H2O (10 mL) and extracted with CH2Cl2 (15 mL  3). The combined
organic layers were dried over anhydrous Na2SO4 and concentrated in vacuo. The
crude product was purified by column chromatography on silica gel (petroleum ether /
EtOAc = 6:1).

3. General procedure for the preparation of compounds 5a-j

To an oven-dried 10 ml Schlenk tube equipped with a magnetic stirring bar were
added sequentially indole 1e or 1f (0.25 mmol), sulfonyl azides 2 (0.5 mmol), and
DMSO (0.5 mL). The reaction mixture was stirred at 50 oC for 48 or 96 hours. The
reaction was quenched by H2O (10 mL) and extracted with CH2Cl2 (15 mL  3). The
combined organic layers were dried over anhydrous Na2SO4 and concentrated in
vacuo. The crude residue was purified by column chromatography on silica gel
(petroleum ether / EtOAc = 6:1) to afford corresponding products 5a-j.

4. Gener al procedure for the preparation of compounds 7a-t

5 
 
To an oven-dried Schlenk tube equipped with a magnetic stirring bar were added
sequentially 3 (0.25 mmol, 1.0 equiv), Rh2(oct)4 (2 mg, 0.0025 mmol), amine 6 (0.5
mmol) and toluene (2.5 mL) under N2 atmosphere. The reaction vessel was placed in
an oil bath preheated to 110 °C. The resulting solution was heated at this temperature
for 2.5 hours. After cooled to room temperature, the reaction solution was
concentrated in vacuo, and the crude product was purified through silica gel column
(petroleum ether / EtOAc = 6:1).

5. General procedure for the preparation of compounds 8a-c

The solution of 7o-t (0.25 mmol) in toluene (2 mL) was stirred at 110 °C under O2
atmosphere for 18 hours. After cooled to room temperature, the solvent was removed
in vacuo. The crude product was purified by column chromatography on silica gel
(petroleum ether / EtOAc = 9:1).

6 
 
Analysis Data of Products
(Z)-N-(3-diazo-1-methylindolin-2-ylidene)-4-methylbenzenesulfonamide (3a):
Orange solid;  Yield: 57mg, 70%; M.p. 169.1-170.0 0C;
1
H NMR (400 MHz, CDCl3) δ 7.88 (d, J = 7.7 Hz, 2H),
7.24 (m , 5H), 7.08 (d, J = 7.7 Hz, 1H), 3.45 (s, 3H),
2.41 (s, 3H); 13C NMR (100MHz, CDCl3) δ155.3, 142.4,
140.1, 134.2, 129.3, 126.3, 125.9, 123.0, 118.9, 116.8, 109.7, 29.0, 21.5; IR (neat,cm-1)
2114, 1538, 1470, 1427, 1385, 1142, 1085, 789, 703, 680; HRMS (ESI): calcd for
(C16H14N4O2S+H+): 327.0910, Found: 327.0917.

(Z)-N-(3-diazo-1-ethylindolin-2-ylidene)-4-methylbenzenesulfonamide (3b):
Orange solid; Yield: 48 mg, 56%; M.p. 162.0-163.0 0C;
1
H NMR (400 MHz, CDCl3) δ 7.87 (d, J = 8.3 Hz, 2H),
7.27 (m, 3H), 7.20 (m, 2H), 7.10 (d, J = 7.6 Hz, 1H),
4.02 (q, J = 7.2 Hz, 2H), 2.41 (s, 3H), 1.26 (t, J = 7.2 Hz,
3H); 13C NMR (100 MHz, CDCl3) δ 154.6, 142.3, 140.3, 133.2, 129.3, 126.2, 125.8,
122.9, 119.2, 117.0, 109.7, 37.5, 21.5, 12.8; IR (neat, cm-1) 2115, 1536, 1464, 1376,
1279, 1141, 1084, 815, 766, 669; HRMS (ESI): calcd for (C17H16N4O2S+H+):
341.1067, Found: 341.1063.

(Z)-N-(3-diazo-1-isopropylindolin-2-ylidene)-4-methylbenzenesulfonamide (3c):
Orange solid; Yield: 47 mg, 53%; M.p. 141.0-142.00C; 1H
NMR (400 MHz, CDCl3) δ 7.87 (d, J = 8.3 Hz, 2H), 7.31
– 7.14 (m, 6H), 5.13 – 4.98 (m, 1H), 2.42 (s, 3H), 1.49 (d,
13
J = 6.8 Hz, 6H); C NMR (100 MHz, CDCl3) δ 154.6,
142.3, 140.3, 132.6, 129.3, 126.2, 125.5, 122.5, 119.5, 117.0, 111.7, 46.6, 21.5, 19.6;
IR (neat, cm-1) 2116, 1538, 1467, 1384, 1274, 1141, 1086, 781, 747, 680; HRMS
(ESI): calcd for (C18H18N4O2S+H+): 355.1223, Found: 355.1204.

7 
 
(Z)-N-(1-allyl-3-diazoindolin-2-ylidene)-4-methylbenzenesulfonamide (3d):
Orange solid; Yield: 41 mg, 46%; M.p. 132.1-133.2 0C;
1
H NMR (400 MHz, CDCl3) δ 7.86 (d, J = 8.0 Hz, 2H),
7.23 (m, 5H), 7.07 (d, J = 7.6 Hz, 1H), 5.81 (m, 1H), 5.19
(d, J = 10.3 Hz, 1H), 5.12 (d, J = 17.2Hz, 1H), 4.60 (d, J
= 5.2Hz, 2H), 2.41 (s, 3H); 13C NMR (100 MHz, CDCl3)
δ 154.9, 142.4, 140.1, 133.5, 130.7, 129.3, 126.2, 125.8, 123.0, 118.9, 118.1, 116.9,
110.3, 44.8, 21.5; IR (neat, cm-1) 2118, 1536, 1385, 1284, 1144, 1086, 1014, 790, 709,
667; HRMS (ESI): calcd for (C18H16N4O2S+H+): 353.1067, Found: 353.1052.

(Z)-N-(1-benzyl-3-diazoindolin-2-ylidene)-4-methylbenzenesulfonamide (3e):
N- Orange solid; Yield: 38 mg, 38%; M.p. 153.0-154.0 0C;
N+ 1
H NMR (400 MHz, CDCl3) δ 7.81 (m, 2H), 7.28 – 7.13
N
N S (m, 10H), 7.03 (dd, J = 6.7, 1.6 Hz, 1H), 5.16 (s, 2H),
O
Bn O
2.40 (s, 3H); 13C NMR (100 MHz, CDCl3) δ 155.3, 142.4,
140.1, 135.2, 133.6, 129.3, 128.7, 127.8, 127.4, 126.3, 125.9, 123.1, 119.0, 116.9,
110.5, 46.1, 21.5; IR (neat, cm-1) 2114, 1538, 1495, 1387, 1272, 1143, 1086, 886, 789,
706; HRMS (ESI): calcd for (C22H18N4O2S+H+): 403.1223, Found: 403.1198.

(Z)-N-(3-diazoindolin-2-ylidene)-4-methylbenzenesulfonamide (3f):
0
N- Orange solid; Yield: 23 mg, 29%; M.p. 185 C
N+
(decomposed); 1H NMR (400 MHz, CDCl3) δ 10.05 (s,
N 1H), 7.88 (d, J = 8.3 Hz, 2H), 7.31 – 7.21 (m, 4H), 7.20
N S
O 13
H O – 7.12 (m, 2H), 2.41 (s, 3H); C NMR (100 MHz,
CDCl3) δ 159.7, 142.9, 139.5, 132.5, 129.4, 126.4, 126.3, 123.4, 117.9, 116.6, 111.9,
21.5; IR (neat, cm-1) 2099, 1574, 1401, 1341, 1247, 1136, 1081, 827, 742; HRMS
(ESI): calcd for (C15H12N4O2S+H+): 313.0754, Found: 313.0744.
(Z)-N-(3-diazo-5-fluoro-1-methylindolin-2-ylidene)-4-methylbenzenesulfonamide
(3g):

8 
 
 Orange solid; Yield: 31 mg, 36%; M.p. 211.4-212.9
0
C; 1H NMR (400 MHz, CDCl3) δ 7.88 (d, J = 8.3 Hz,
2H), 7.29 (d, J = 8.0 Hz, 2H), 7.03 – 6.93 (m, 3H),
13
3.44 (s, 3H), 2.42 (s, 3H); C NMR (100 MHz,
CDCl3) δ 160.6, 158.2, 155.2, 142.6, 140.0, 130.5, 129.4, 126.3, 120.3 (d, J C-F = 10.6
Hz), 112.9 (d, J C-F = 24.5 Hz), 110.3 (d, J C-F = 9.0 Hz), 104.3 (d, J C-F = 27.3 Hz),
29.2, 21.5; IR( neat, cm-1) 2148, 1557, 1426, 1394, 1253, 1081, 938, 808, 769, 680;
HRMS (ESI): calcd for (C16H13FN4O2S+H+): 345.0816, Found: 345.0802.

(Z)-N-(5-chloro-3-diazo-1-methylindolin-2-ylidene)-4-methylbenzenesulfonamide
(3h):
Orange solid; Yield: 31 mg, 36%; M.p.
227.4-228.10C; 1H NMR (400 MHz, CDCl3) δ 7.88
(d, J = 8.4Hz, 2H), 7.29 (d, J = 8.0 Hz, 2H), 7.27 –
7.19 (m, 2H), 6.99 (d, J = 8.4 Hz, 1H), 3.43 (s, 3H),
2.42 (s, 3H); 13C NMR (100 MHz, CDCl3) δ 155.1, 142.6, 139.8, 132.8, 129.4, 128.7,
126.4, 126.0, 120.5, 116.8, 110.4, 29.2, 21.5; IR (neat, cm-1) 2139, 1726, 1545, 1386,
1285, 1255, 1127, 1073, 810, 733, 682; HRMS (ESI): calcd for (C16H13ClN4O2S+H+):
361.0521, Found: 361.0501.

(Z)-N-(5-bromo-3-diazo-1-methylindolin-2-ylidene)-4-methylbenzenesulfonamide
(3i):
Orange solid; Yield: 52 mg, 51%; M.p. 195 0C
(decomposed); 1H NMR (400 MHz, CDCl3) δ 7.87 (d,
J = 8.3 Hz, 2H), 7.38 (dd, J = 8.4, 1.6 Hz, 1H), 7.35
(d, J = 1.7 Hz, 1H), 7.30 (d, J = 8.0Hz, 2H), 6.94 (d,
J = 8.4Hz, 1H), 3.43 (s,3H), 2.42 (s, 3H); 13C NMR (100 MHz, CDCl3) δ 154.9, 142.7,
139.8, 133.2, 129.4, 128.7, 126.4, 120.9, 119.6, 115.7, 110.8, 29.2, 21.5; IR (neat,

9 
 
cm-1) 2142, 1563, 1389, 1256, 1141, 1060, 907, 808, 729, 706; HRMS (ESI): calcd
for (C16H13BrN4O2S+H+): 405.0015, Found: 404.9987.

(Z)-N-(3-diazo-5-methoxy-1-methylindolin-2-ylidene)-4-methylbenzenesulfonami
de (3j):
Orange solid; Yield: 69 mg, 78%; M.p. 196.8-197.5
0
C; 1H NMR (400 MHz, CDCl3) δ 7.88 (d, J = 8.3
Hz, 2H), 7.28 (d, J = 8.0 Hz, 2H), 6.98 (d, J = 8.7
Hz, 1H), 6.84 (dd, J = 8.7, 2.4 Hz, 1H), 6.76 (d, J =
2.3 Hz, 1H), 3.84 (s, 3H), 3.43 (s, 3H), 2.41 (s, 3H); 13C NMR (100 MHz, CDCl3) δ
156.5, 155.0, 142.3, 140.3, 129.3, 128.3, 126.3, 120.1, 112.3, 110.3, 102.5, 55.9, 29.1,
21.5; IR (neat, cm-1) 2137, 1584, 1488, 1430, 1392, 1256, 1081, 831, 771, 681;
HRMS (ESI): calcd for (C17H16N4O3S+H+): 357.1016, Found: 357.1005.

(Z)-N-(7-bromo-3-diazo-1-methylindolin-2-ylidene)-4-methylbenzenesulfonamide
(3k):

N- Orange solid; Yield: 25mg, 25%; M.p. 177.3-178.00C; 1H

N+
NMR (400 MHz, CDCl3) δ 7.88 (d, J = 8.0 Hz, 2H), 7.40
N (dd, J = 8.0, 0.8 Hz, 1H), 7.30 (d, J = 8.1 Hz, 2H), 7.14
N S
O
Br O (dd, J = 7.6, 0.8 Hz, 1H), 7.03 (t, J = 7.8 Hz, 1H), 3.85 (s,
3H), 2.43 (s, 3H); 13C NMR (100 MHz, CDCl3) δ 155.7, 142.6, 139.9, 131.4, 131.3,
129.4, 126.4, 123.8, 121.8, 115.7, 104.1, 32.4, 21.5; IR (neat, cm-1) 2113, 1548, 1414,
1382, 1273, 1145, 1123, 1086, 809, 693; HRMS (ESI): calcd for
(C16H13BrN4O2S+H+): 405.0015, Found: 404.9991.

(Z)-N-(3-diazo-1,7-dimethylindolin-2-ylidene)-4-methylbenzenesulfonamide
(3l):
Orange solid; Yield: 50 mg, 59%; M.p. 163.9-164.5 0C;
1
H NMR (400 MHz, CDCl3) δ 7.88 (d, J = 8.3 Hz, 2H),

10 
 
7.28 (d, J = 8.0 Hz, 2H), 7.09 – 6.97 (m, 3H), 3.73 (s, 3H), 2.64 (s, 3H), 2.41 (s, 3H);
13
C NMR (100 MHz, CDCl3) δ 155.7, 142.3, 140.3, 132.6, 129.6, 129.3, 126.3, 122.9,
121.7, 119.4, 114.8, 32.3, 21.5, 19.6; IR (neat, cm-1) 2110, 1538, 1445, 1410, 1377,
1269, 1143, 1129, 1081, 925, 771, 700; HRMS (ESI): calcd for (C17H16N4O2S+H+):
341.1067, Found: 341.1037.

(Z)-N-(3-diazo-1-methylindolin-2-ylidene)benzenesulfonamide (3m):
Orange solid; Yield: 50 mg, 65%; M.p. 152.0-153.1 0C; 1H
NMR (400 MHz, CDCl3) δ 8.07 – 7.96 (m, 2H), 7.58 – 7.45
(m, 3H), 7.32 – 7.17 (m, 3H), 7.09 (d, J = 7.6 Hz, 1H), 3.47
(s, 3H); 13C NMR (100 MHz, CDCl3) δ 155.4, 143.0, 134.2,
131.8, 128.7, 126.3, 125.9, 123.1, 118.9, 116.9, 109.8, 29.1; IR (neat, cm-1) 2113,
1534, 1470, 1382, 1271, 1142, 1085, 1011, 797, 748; HRMS (ESI): calcd for
(C15H12N4O2S+H+): 313.0754, Found: 313.0758.

(Z)-N-(3-diazo-1-methylindolin-2-ylidene)naphthalene-2-sulfonamide (3n):
Orange solid; Yield: 56 mg, 62%; M.p. 158.3-159.0 0C;
1
H NMR (400 MHz, CDCl3) δ 8.53 (s, 1H), 8.01 (dd, J
= 8.4, 1.7 Hz, 1H), 7.95 (t, J = 7.1 Hz, 2H), 7.89 (d, J =
7.2Hz, 1H), 7.63 – 7.55 (m, 2H), 7.31 – 7.17 (m, 3H),
7.08 (d, J = 7.9 Hz, 1H), 3.46 (s, 3H); 13C NMR (100 MHz, CDCl3) δ 155.3, 139.9,
134.5, 134.2, 132.2, 129.2, 129.0, 128.3, 127.8, 127.2, 126.8, 125.9, 123.1, 122.5,
118.9, 116.9, 109.8, 29.1; IR (neat, cm-1) 2114, 1542, 1470, 1427, 1384, 1274, 1126,
1073, 794, 747, 703; HRMS (ESI): calcd for (C19H14N4O2S+H+): 363.0910, Found:
363.0917.

(Z)-N-(3-diazo-1-methylindolin-2-ylidene)-4-methoxybenzenesulfonamide (3o):
Orange solid; Yield: 28 mg, 32%; M.p. 134.5-135.2
0
C; 1H NMR (400 MHz, CDCl3) δ 7.93 (m, 2H),

11 
 
7.35 – 7.16 (m, 3H), 7.08 (d, J = 7.9 Hz, 1H), 6.96 (m, 2H), 3.86 (s, 3H), 3.45 (s, 3H);
13
C NMR (100 MHz, CDCl3) δ 162.2, 155.2, 134.9, 134.2, 128.3, 125.9, 123.0, 118.9,
116.9, 113.9, 109.7, 55.5, 29.0; IR (neat, cm-1) 2112, 1538, 1497, 1384, 1256, 1141,
1086, 808, 789; HRMS (ESI): calcd for (C16H14N4O3S+H+): 343.0859, Found:
343.0861.

(Z)-N-(3-diazo-1-methylindolin-2-ylidene)methanesulfonamide (3p):
Orange solid; Yield: 20 mg, 32%; M.p. 167.0-167.8 0C; 1H
NMR (400 MHz, CDCl3) δ 7.29 (m, 1H), 7.21 (m, 2H), 7.09 (d,
J = 7.9 Hz, 1H), 3.46 (s, 3H), 3.17 (s, 3H); 13C NMR (100 MHz,
CDCl3) δ 155.4, 134.2, 125.8, 122.9, 118.6, 116.9, 109.6, 42.5,
28.7; IR (neat, cm-1) 2945, 2116, 1539, 1383, 1256, 1112, 1035, 958, 810, 748;
HRMS (ESI): calcd for (C10H10N4O2S+H+): 251.0597, Found: 251.0609.

(Z)-N-(3-diazo-1-methylindolin-2-ylidene)-4-nitrobenzenesulfonamide (3q)
Orange solid; Yield: 10 mg, 10%; M.p. 191 0C
(decomposed); 1H NMR (400 MHz, DMSO-d6) δ 8.38
(m, 2H), 8.16 (m, 2H), 7.61 (d, J = 7.3 Hz, 1H), 7.45
(d, J = 7.9 Hz, 1H), 7.37-7.33 (m, 1H), 7.28-7.24 (m, 1H), 3.47 (s, 1H); 13C NMR
(100 MHz, DMSO-d6) δ 155.2, 149.3, 148.8, 133.7, 127.4, 126.0, 124.7, 123.2, 118.7,
118.4, 110.9, 29.4; HRMS (ESI): calcd for (C15H11N5O4S+H+): 358.0605, Found:
358.0610.

(Z)-4-methyl-N-(1-methylindolin-2-ylidene)benzenesulfonamide (4a):
Orange solid; Yield: 5 mg, 7%; M.p. 168.2-169.9 0C; 1H
NMR (400 MHz, CDCl3) δ 7.89 (d, J = 8.4 Hz, 2H), 7.31
(m, 4H), 7.12 (t, J = 7.6 Hz, 1H), 6.95 (d, J = 8.0 Hz,
1H), 4.22 (s, 2H), 3.36 (s, 3H), 2.41 (s, 3H); 13C NMR
(100 MHz, CDCl3) δ 169.7, 143.9, 142.7, 139.4, 129.3, 128.1, 126.7, 126.3, 124.4,

12 
 
123.7, 109.1, 36.2, 28.5, 21.5; IR (neat, cm-1) 2931, 1574, 1371, 1276, 1147, 1093,
1076, 855, 779, 753, 686; HRMS (EI): calcd for C16H16N2O2S: 300.0932, Found:
300.0937.

(Z)-N-(1-methylindolin-2-ylidene)-4-nitrobenzenesulfonamide (4b):
Orange solid; Yield: 25 mg, 30%; M.p. 222.2-222.9
0
C; 1H NMR (400 MHz, CDCl3) δ 8.40 – 8.31 (m,
2H), 8.22 – 8.14 (m, 2H), 7.36 (m, 2H), 7.18 (t, J =
7.4 Hz, 1H), 7.00 (d, J = 7.6 Hz, 1H), 4.29 (s, 2H),
3.38 (s, 3H); 13C NMR (100 MHz, CDCl3) δ 170.0, 149.7, 148.1, 143.6, 128.3, 127.9,
126.1, 124.5, 124.3, 124.0, 109.5, 36.7, 28.7; IR (neat, cm-1) 1555, 1519, 1367, 1345,
1275, 1137, 1070, 980, 850, 781, 744; HRMS (EI): calcd for C15H13N3O4S: 331.0627,
Found: 331.0629.

N-(1,3-dimethyl-1H-indol-2-yl)-4-methylbenzenesulfonamide (4c'):
White solid; Yield: 69 mg, 87%; M.p. 132.8-133.5 0C;
1
H NMR (400 MHz, DMSO-d6) δ 10.08 (s, 1H), 7.57 (d,
J = 8.0 Hz, 2H), 7.42 – 7.35 (m, 3H), 7.33 (d, J = 8.0 Hz,
1H), 7.18 – 7.12 (m, 1H), 7.04 – 6.97 (m, 1H), 3.50 (s,
3H), 2.39 (s, 3H), 1.56 (s, 3H). 13C NMR (100 MHz, DMSO-d6) δ 143.5, 137.5, 134.5,
129.8, 127.8, 127.0, 126.2, 122.0, 118.8, 118.7, 109.7, 105.9, 29.0, 21.1, 7.5; IR (neat,
cm-1) 2923, 1566, 1468, 1275, 1144, 1082, 946, 818, 747, 768; HRMS (EI): calcd for
C17H18N2O2S: 314.1089, Found: 314.1086.

N-(1,3-dimethyl-1H-indol-2-yl)benzenesulfonamide (4d'):
White solid; Yield: 68 mg, 90%; M.p. 88.5-89.4 0C; 1H
NMR (400 MHz, DMSO-d6) δ 10.17 (s, 1H), 7.70 (m, 3H),
7.62 – 7.55 (m, 2H), 7.37 (d, J = 7.6 Hz, 1H), 7.33 (d, J =
8.4 Hz, 1H), 7.16 (t, J = 7.6 Hz, 1H), 7.00 (t, J = 7.4 Hz,

13 
 
1H), 3.50 (s, 3H), 1.53 (s, 3H); 13C NMR (100 MHz, DMSO-d6) δ 140.2, 134.6, 133.2,
129.5, 127.7, 127.0, 126.2, 122.0, 118.9, 118.7, 109.8, 105.9, 29.0, 7.4; IR (neat, cm-1)
2924, 1564, 1469, 1277, 1144, 1081, 947, 779, 750, 689; HRMS (EI): calcd for
C16H16N2O2S: 300.0932, Found: 300.0936.

(Z)-N-(1,3-dimethylindolin-2-ylidene)naphthalene-2-sulfonamide (4e):
White solid; Yield: 82 mg, 94%; M.p. 155.3-156.3 0C;
1
H NMR (400 MHz, CDCl3) δ 8.54 (s, 1H), 8.00 (dd, J
= 8.6, 1.8 Hz, 1H), 7.95 (m, 2H), 7.91 – 7.86 (m, 1H),
7.62 – 7.55 (m, 2H), 7.35 – 7.28 (m, 2H), 7.18 – 7.12 (m, 1H), 6.93 (d, J = 7.8 Hz,
1H), 4.63 (q, J = 7.4 Hz, 1H), 3.29 (s, 3H), 1.78 (d, J = 7.4 Hz, 3H); 13C NMR (100
MHz, CDCl3) δ 173.1, 142.4, 140.2, 134.5, 133.0, 132.1, 129.2, 128.8, 128.2, 128.0 ,
127.8, 127.1, 126.7, 123.8, 123.5, 122.6, 109.1, 42.3 , 28.5, 19.6; IR (neat, cm-1) 2928,
1563, 1495, 1468, 1391, 1280, 1126, 1071, 955, 749, 675; HRMS (EI): calcd for
C20H18N2O2S: 350.1089, Found: 350.1091.

N-(1,3-dimethyl-1H-indol-2-yl)naphthalene-2-sulfonamide (4e'):
White solid; Yield: 82 mg, 94%; M.p. 155.3-156.3 0C;
1
H NMR (400 MHz, DMSO-d6) δ 10.30 (s, 1H), 8.33
(d, J = 1.2Hz, 1H), 8.17 (d, J = 8.8 Hz, 1H), 8.12 (d, J
= 8.0 Hz, 1H), 8.08 (d, J = 8.0 Hz, 1H), 7.81 (dd, J =
8.7, 2.0 Hz, 1H), 7.72 (m, 1H), 7.65 (m, 1H), 7.33 (dd, J = 8.4, 2.8 Hz, 2H), 7.15 (m,
13
1H), 6.98 (m, 1H), 3.53 (s, 3H), 1.44 (s, 3H); C NMR (100 MHz, DMSO-d6) δ
137.5, 134.6, 134.5, 131.9, 129.6, 129.4, 129.1, 128.0, 128.0, 127.8, 127.7, 126.2,
122.6, 122.0, 118.9, 118.8, 109.8, 106.0, 29.0, 7.5; IR (neat, cm-1) 2928, 1563, 1495,
1468, 1391, 1280, 1126, 1071, 955, 749, 675; HRMS (EI): calcd for C20H18N2O2S:
350.1089, Found: 350.1091.

N-(1,3-dimethyl-1H-indol-2-yl)-4-methoxybenzenesulfonamide (4f'):

14 
 
 White solid; Yield: 73 mg, 89%; M.p. 158.8-159.2
0
C; 1H NMR (400 MHz, DMSO-d6) δ 9.98 (s, 1H),
7.60 (d, J = 8.9 Hz, 2H), 7.37 (d, J = 7.6 Hz, 1H),
7.33 (d, J = 8.0 Hz, 1H), 7.18 – 7.12 (m, 1H), 7.12
– 7.06 (m, 2H), 7.03 – 6.97 (m, 1H), 3.83 (s, 3H), 3.50 (s, 3H), 1.58 (s, 3H); 13C NMR
(100 MHz, DMSO-d6) δ 162.8, 134.5, 131.9, 129.2 , 128.0, 126.2, 121.9, 118.8, 118.7,
114.5, 109.7, 105.7 , 55.8, 28.9 , 7.5; IR (neat, cm-1) 2923, 1568, 1495, 1466, 1259,
1155, 1086, 829, 738, 677; HRMS (EI): calcd for C17H18N2O3S: 330.1038, Found:
330.1039.
(Z)-N-(1,3-dimethylindolin-2-ylidene)-4-nitrobenzenesulfonamide (4g):
yellow solid; Yield: 72 mg, 84%; M.p. 177.9-178.4
0
C; 1H NMR (400 MHz, CDCl3) δ 8.34 (m, 2H), 8.18
(m, 2H), 7.35 (t, J = 7.6 Hz, 2H), 7.20 (m, 1H), 6.99
(d, J = 7.8 Hz, 1H), 4.57 (q, J = 7.4 Hz, 1H), 3.33 (s,
3H), 1.75 (d, J = 7.2 Hz, 3H). 13C NMR (100 MHz, CDCl3) δ 173.7, 149.5, 148.9,
142.2, 132.9, 128.2, 127.7, 124.4, 124.0, 123.6, 109.5, 42.7, 28.6, 19.4; IR (neat, cm-1)
1569, 1555, 1524, 1347, 1283, 1144, 1078, 949, 821, 781, 750, 738; HRMS (EI):
calcd for C16H15N3O4S: 345.0783, Found: 345.0788.

N-(1,3-dimethyl-1H-indol-2-yl)-4-nitrobenzenesulfonamide (4g'):
yellow solid; Yield: 72 mg, 84%; M.p. 177.9-178.4
NO2 0
C; 1H NMR (400 MHz, DMSO-d6) δ 10.60 (s, 1H),
NH
N S 8.45 – 8.40 (m, 2H), 7.98 – 7.93 (m, 2H), 7.39 (d, J
O
O
= 7.6 Hz, 1H), 7.36 (d, J = 8.3 Hz, 1H), 7.18 (m, 1H),
13
7.04 – 6.99 (m, 1H), 3.52 (s, 3H), 1.57 (s, 3H); C NMR (100 MHz, DMSO-d6) δ
150.1, 145.8, 134.7, 128.7, 126.9, 126.1, 124.8, 122.3, 119.0, 118.9, 109.9, 106.2,
29.1, 7.7; IR (neat, cm-1) 1569, 1555, 1524, 1347, 1283, 1144, 1078, 949, 821, 781,
750, 738; HRMS (EI): calcd for C16H15N3O4S: 345.0783, Found: 345.0788.

15 
 
 (E)-N-(1-ethyl-3-methylindolin-2-ylidene)naphthalene-2-sulfonamide (4h):
White solid; Yield: 76 mg, 83%; M.p. 160.4-161.2 0C;
1
N H NMR (400 MHz, CDCl3) δ 8.54 (s, 1H), 7.94 (m,
N S
O 4H), 7.64 – 7.55 (m, 2H), 7.32 (m, 2H), 7.15 (t, J =
O

7.4 Hz, 1H), 6.95 (d, J = 7.8 Hz, 1H), 4.63 (q, J = 7.4
Hz, 1H), 3.85 (m, 2H), 1.77 (d, J = 7.4 Hz, 3H), 1.20 (t, J = 7.2 Hz, 3H); 13C NMR
(100 MHz, CDCl3) δ 172.5, 141.4, 140.3, 134.4, 133.3, 132.1, 129.2, 128.8, 128.1,
127.9, 127.7, 127.1, 126.5, 123.7, 123.6, 122.5, 109.2, 42.3, 36.8, 19.7, 11.9; IR (neat,
cm-1) 2933, 1559, 1464, 1405, 1290, 1145, 1072, 967, 923, 860, 820, 756, 673;
HRMS (EI): calcd for C21H20N2O2S: 364.1245, Found: 364.1244.

N-(1-ethyl-3-methyl-1H-indol-2-yl)naphthalene-2-sulfonamide (4h'):
White solid; Yield: 76 mg, 83%; M.p. 160.4-161.2 0C;
1
NH
H NMR (400 MHz, DMSO-d6) δ 10.29 (s, 1H), 8.34
N S
O (s, 1H), 8.18 (d, J = 8.7 Hz, 1H), 8.12 (d, J = 8.4 Hz,
O
1H), 8.08 (d, J = 8.0 Hz, 1H), 7.83 (dd, J = 8.7, 2.0
Hz, 1H), 7.76 – 7.70 (m, 1H), 7.65 (t, J = 7.5 Hz, 1H), 7.38 (d, J = 8.4 Hz, 1H), 7.31
(d, J = 8.0Hz, 1H), 7.17 – 7.12 (m, 1H), 6.97 (t, J = 7.4 Hz, 1H), 4.15 (q, J = 7.0 Hz,
2H), 1.37 (s, 3H), 1.19 (t, J = 7.1 Hz, 3H); 13C NMR (100 MHz, DMSO-d6) δ 137.6,
134.4, 133.5, 131.9, 129.6, 129.4, 129.1, 128.0, 127.9, 127.8, 126.9, 126.4, 122.6,
122.1, 118.9, 118.8, 109.9, 106.3, 36.8, 14.8, 7.5 ; IR (neat, cm-1) 2933, 1559, 1464,
1405, 1290, 1145, 1072, 967, 923, 860, 820, 756, 673; HRMS (EI): calcd for
C21H20N2O2S: 364.1245, Found: 364.1244.

N-(1-benzyl-3-methyl-1H-indol-2-yl)naphthalene-2-sulfonamide (4i'):
White solid; Yield: 68 mg, 64%; M.p. 154.7-155.1 0C;
1
H NMR (400 MHz, DMSO-d6) δ 10.43 (s, 1H), 8.33
(d, J =0.8 Hz, 1H), 8.17 (d, J = 8.7 Hz, 1H), 8.12 (d, J
= 8.1 Hz, 1H), 8.07 (d, J = 8.4 Hz, 1H), 7.82 (dd, J =

16 
 
8.4, 1.6 Hz, 1H), 7.73 (t, J = 7.5 Hz, 1H), 7.65 (t, J = 7.5 Hz, 1H), 7.25 (m, 5H), 7.08
(t, J = 7.7 Hz, 1H), 7.02 (d, J = 7.1 Hz, 2H), 6.96 (t, J = 7.5 Hz, 1H), 5.46 (s, 2H),
1.32 (s, 3H); 13C NMR (100 MHz, DMSO-d6) δ 138.4, 137.3, 134.5, 134.2, 131.8,
129.6, 129.4, 129.1, 128.5, 128.1, 128.0, 127.8, 127.7, 127.1, 126.7, 126.5, 122.6,
122.3, 119.1, 118.9, 110.5, 106.6, 45.4, 7.4; IR (neat, cm-1) 1562, 1465, 1333, 1275,
1148, 1126, 1071, 818, 746, 669; HRMS (EI): calcd for C26H22N2O2S: 426.1402,
Found: 426.1400.

N-(1,2-dimethyl-1H-indol-3-yl)-4-methylbenzenesulfonamide (5a):
White solid; Yield: 71 mg, 90%; M.p. 183.7-184.5 0C; 1H NMR
O (400 MHz, DMSO-d6) δ 9.26 (s, 1H), 7.51 (d, J = 8.0 Hz, 2H),
S
O NH 7.31 (d, J = 8.4 Hz, 1H), 7.28 (d, J = 8.1 Hz, 2H), 6.99 (t, J =
7.6 Hz, 1H), 6.94 (d, J = 8.0 Hz, 1H), 6.80 (t, J = 7.4 Hz, 1H),
N
13
3.58 (s, 3H), 2.34 (s, 3H), 2.01 (s, 3H); C NMR (100 MHz,
DMSO-d6) δ 142.6, 138.1, 134.9, 134.6, 129.4, 127.0, 124.9, 120.6, 118.9, 117.4,
109.2, 108.0, 29.6, 21.1, 9.3; IR (neat, cm-1) 2923, 1596, 1472, 1402, 1372, 1311,
1157, 1093, 739, 673; HRMS (EI): calcd for C17H18N2O2S: 314.1089, Found:
314.1092.

N-(1,2-dimethyl-1H-indol-3-yl)benzenesulfonamide (5b):
White solid; Yield: 68 mg, 90%; M.p. 213.1-213.4 0C; 1H NMR
(400 MHz, CDCl3) δ 7.71 (d, J = 7.3 Hz, 2H), 7.51 (t, J = 7.5 Hz,
1H), 7.35 (t, J = 7.8 Hz, 2H), 7.19 (d, J = 8.2 Hz, 1H), 7.06 (t, J
= 7.6 Hz, 1H), 6.83 (t, J = 7.4 Hz, 1H), 6.71 (d, J = 7.9 Hz, 1H),
13
6.18 (s, 1H), 3.61 (s, 3H), 2.23 (s, 3H); C NMR (100 MHz,
CDCl3) δ 140.2, 136.5, 134.9, 132.5, 128.8, 127.4, 124.8, 121.1, 119.7, 116.8, 108.7,
107.1, 29.7, 9.6; IR (neat, cm-1) 3057, 2935, 1535, 1470, 1375, 1313, 1160, 1092, 739,
694; HRMS (EI): calcd for C16H16N2O2S: 300.0932, Found: 300.0931.

17 
 
N-(1,2-dimethyl-1H-indol-3-yl)naphthalene-2-sulfonamide (5c):
White solid; Yield: 81 mg, 93%; M.p. 223.8-224.3 0C; 1H NMR
(400 MHz, CDCl3) δ 8.25 (s, 1H), 7.90 – 7.83 (m, 2H), 7.80 –
7.74 (m, 2H), 7.61 (t, J = 7.5 Hz, 1H), 7.53 (t, J = 7.5 Hz, 1H),
7.18 (d, J = 8.4 Hz, 1H), 7.02 (t, J = 7.5 Hz, 1H), 6.77 (d, J = 7.7
Hz, 1H), 6.71 (t, J = 7.4 Hz, 1H), 6.23 (s, 1H), 3.60 (s, 3H), 2.19
(s, 3H); 13C NMR (100 MHz, CDCl3) δ 137.3, 136.5, 134.9, 134.7,
132.1, 129.2, 129.0, 128.7, 128.6, 127.8, 127.3, 124.9, 122.8, 121.2, 119.7, 116.9,
108.7, 107.1, 29.8, 9.7; IR (neat, cm-1) 2922, 1588, 1471, 1403, 1372, 1252, 1158,
1131, 744, 675; HRMS (EI): calcd for C20H18N2O2S: 350.1089, Found: 350.1085.

N-(1,2-dimethyl-1H-indol-3-yl)-4-methoxybenzenesulfonamide (5d):
White solid; Yield: 73mg, 89%; M.p. 190.5-190.80C; 1H
NMR (400 MHz, CDCl3) δ 7.63 (d, J = 8.7 Hz, 2H), 7.21 (d,
J = 8.1 Hz, 1H), 7.08 (t, J = 7.4 Hz, 1H), 6.92 – 6.70 (m,
4H), 6.02 (s, 1H), 3.82 (s, 3H), 3.64 (s, 3H), 2.27 (s, 3H);
13
C NMR (100 MHz, CDCl3) δ 162.9, 136.5, 134.9, 132.0,
129.5, 124.9, 121.1, 119.7, 116.9, 114.0, 108.7, 107.3, 55.6, 29.8, 9.7; IR (neat, cm-1)
2956, 1594, 1469, 1403, 1315, 1258, 1154, 1096, 743, 683; HRMS (EI): calcd for
C17H18N2O3S: 330.1038, Found: 330.1043.

N-(1,2-dimethyl-1H-indol-3-yl)-4-nitrobenzenesulfonamide (5e):
yellow solid; Yield: 74 mg, 86%; M.p. 211.3-211.7 0C; 1H
NMR (400 MHz, DMSO-d6) δ 9.76 (s, 1H), 8.32 (d, J = 8.9
Hz, 2H), 7.88 (d, J = 8.9 Hz, 2H), 7.34 (d, J = 8.2 Hz, 1H),
7.00 (m, 1H), 6.89 (d, J = 7.7 Hz, 1H), 6.81 (t, J = 7.4 Hz,
13
1H), 3.60 (s, 3H), 2.05 (s, 3H); C NMR (100 MHz,

18 
 
DMSO-d6) δ 149.6, 146.5, 135.2, 134.6, 128.6, 124.5, 124.4, 120.8, 119.1, 117.0,
109.4, 107.0, 29.7, 9.4; IR (neat, cm-1) 3099, 2919, 1604, 1524, 1344, 1308, 1160, 855,
759, 733, 684; HRMS (EI): calcd for C16H15N3O4S: 345.0783, Found: 345.0788.

4-methyl-N-(1-methyl-2-phenyl-1H-indol-3-yl)benzenesulfonamide (5f):
yellow solid; Yield: 69 mg, 74%; M.p. 225.5-225.9 0C; 1H NMR
(400 MHz, CDCl3) δ 7.65 (d, J = 7.9 Hz, 1H), 7.37 – 7.21 (m,
7H), 7.15 (m, 1H), 6.97 (d, J = 8.0 Hz, 2H), 6.93 (dd, J = 8.0, 1.3
Hz, 2H), 6.39 (s, 1H), 3.50 (s, 3H), 2.36 (s, 3H); 13C NMR (100
MHz, CDCl3) δ 142.9, 137.5, 136.1, 135.5, 129.9, 129.2, 129.1,
128.3, 127.4, 125.2, 122.5, 120.5, 119.4, 109.4, 108.7, 30.9, 21.5; IR (neat, cm-1) 2922,
1599, 1465, 1364, 1321, 1157, 1092, 742, 700, 662; HRMS (EI): calcd for
C22H20N2O2S: 376.1245, Found: 376.1250.

N-(1-methyl-2-phenyl-1H-indol-3-yl)benzenesulfonamide (5g):
yellow solid; Yield: 70 mg, 74%; M.p. 213.1-213.4 0C; 1H NMR
(400 MHz, CDCl3) δ 7.60 (d, J = 8.0 Hz, 1H), 7.49 – 7.39 (m, 3H),
7.37 – 7.18 (m, 7H), 7.17 -7.11(m, H), 6.94 (dd, J = 8.1, 1.3Hz, 2H),
13
6.38 (s, 1H), 3.51 (s, 3H); C NMR (100 MHz, CDCl3) δ 139.2,
137.6, 135.5, 132.3, 130.0, 129.1, 128.6, 128.5, 128.4, 127.4, 125.1,
122.5, 120.5, 119.3, 109.4, 108.5, 30.9; IR (neat, cm-1) 3058, 1579, 1467, 1446, 1362,
1315, 1158, 1092, 745, 691; HRMS (EI): calcd for C21H18N2O2S: 362.1089, Found:
362.1094.

N-(1-methyl-2-phenyl-1H-indol-3-yl)naphthalene-2-sulfonamide (5h):
yellow solid; Yield: 81 mg, 79%; M.p. 208.4-209.1 0C; 1H NMR
(400 MHz, CDCl3) δ 8.00 (s, 1H), 7.82 (d, J = 8.2 Hz, 1H), 7.76
(d, J = 7.9 Hz, 1H), 7.69 (d, J = 8.1 Hz, 1H), 7.57 (m, 3H), 7.39
(dd, J = 8.7, 1.7 Hz, 1H), 7.29 (m, 2H), 7.17 (t, J = 7.3 Hz, 1H),

19 
 
7.11 (t, J = 7.5 Hz, 1H), 6.94 (t, J = 7.7 Hz, 2H), 6.70 (d, J = 7.1 Hz, 2H), 6.57 (s, 1H),
3.43 (s, 3H); 13C NMR (100 MHz, CDCl3) δ 137.6, 136.0, 135.5, 134.7, 131.9, 129.6,
129.2, 128.9, 128.7, 128.6, 128.5, 128.2, 128.1, 127.6, 127.0, 125.4, 122.6, 122.6,
120.6, 119.4, 109.4, 108.4, 30.8; IR (neat, cm-1) 3056, 2925, 1467, 1319, 1260, 1157,
1129, 1076, 746, 701, 659; HRMS (EI): calcd for C25H20N2O2S: 412.1245, Found:
412.1255.

4-methoxy-N-(1-methyl-2-phenyl-1H-indol-3-yl)benzenesulfonamide (5i):
yellow solid; Yield: 59 mg, 60%; M.p. 200.1-200.9 0C; 1H
NMR (400 MHz, CDCl3) δ 7.66 (d, J = 7.9 Hz, 1H), 7.41 –
7.22 (m, 7H), 7.16 (t, J = 7.3 Hz, 1H), 6.97 (d, J = 6.8 Hz,
2H), 6.64 (d, J = 8.7 Hz, 2H), 6.31 (s, 1H), 3.82 (s, 3H), 3.51
(s, 3H); 13C NMR (100 MHz, CDCl3) δ 162.7, 137.5, 135.6,
130.8, 130.0, 129.4, 129.3, 128.4, 128.4, 125.2, 122.6, 120.5, 119.5, 113.7, 109.4,
108.8, 55.5, 30.9; IR (neat, cm-1) 2925, 1597, 1496, 1466, 1317, 1257, 1153, 1094,
1025, 745, 702; HRMS (EI): calcd for C22H20N2O3S: 392.1195, Found: 392.1192.

N-(1-methyl-2-phenyl-1H-indol-3-yl)-4-nitrobenzenesulfonamide (5j):
yellow solid; Yield: 77 mg, 76%; M.p. 208.4-208.9 0C; 1H
NMR (400 MHz, CDCl3) δ 7.90 (d, J = 8.9 Hz, 2H), 7.72 (d, J
= 7.9 Hz, 1H), 7.54 (d, J = 8.9 Hz, 2H), 7.38 – 7.19 (m, 6H),
6.94 (d, J = 7.1 Hz, 2H), 6.78 (s, 1H), 3.52 (s, 3H); 13C NMR
(100 MHz, CDCl3) δ 149.7, 144.8, 137.9, 135.6, 129.7, 128.98,
128.5, 128.5, 128.4, 125.4, 123.5, 123.0, 121.0, 118.9, 109.7,
107.3, 31.0; IR (neat, cm-1) 3060, 2940, 1527, 1346, 1311, 1162, 1091, 853, 738, 702;
HRMS (EI): calcd for C21H17N3O4S: 407.0940, Found: 407.0939.

N-(3-(ethyl(phenyl)amino)-1-methyl-1H-indol-2-yl)-4-methylbenzenesulfonamide
(7a):

20 
 
 White solid; Yield: 101 mg, 96%; M.p. 141.9-142.7 0C; 1H
NMR (400 MHz, CDCl3) δ 7.52 (d, J = 8.0 Hz, 2H), 7.35
(d, J = 8.3 Hz, 1H), 7.28 – 7.23 (m, 1H), 7.19 (d, J = 7.6
Hz, 1H), 7.04 – 6.96 (m, 5H), 6.63 (t, J = 7.2 Hz, 1H),
6.50 (s, 1H), 6.27 (d, J = 8.0 Hz, 2H), 3.83 (s, 3H), 3.12 (q, J = 6.8 Hz, 2H), 2.26 (s,
3H), 1.05 (t, J = 7.1 Hz, 3H). 13C NMR (100 MHz, CDCl3) δ 147.0, 143.9, 136.2,
134.1, 129.3, 128.8, 127.2, 125.4, 123.1, 122.8, 119.7, 119.5, 117.6, 116.8, 113.1,
110.0, 45.8, 30.0, 21.5, 12.9; IR (neat, cm-1) 3057, 2971, 1595, 1496, 1468, 1377,
1325, 1156, 1091, 737, 687, 661; HRMS (ESI): calcd for (C24H25N3O2S+H+):
420.1704, Found: 420.1741.

N-(1-ethyl-3-(ethyl(phenyl)amino)-1H-indol-2-yl)-4-methylbenzenesulfonamide
(7b):
White solid; Yield: 99 mg, 91%; M.p. 169.3-169.8 0C; 1H
NMR (400 MHz, CDCl3) δ 7.52 (d, J = 8.0 Hz, 2H), 7.39
(d, J = 8.3 Hz, 1H), 7.24 (m, 1H), 7.18 (d, J = 7.9 Hz,
1H), 7.04 – 6.94 (m, 5H), 6.62 (t, J = 7.2 Hz, 1H), 6.56 (s,
1H), 6.25 (d, J = 7.6 Hz, 2H), 4.39 (q, J = 7.2 Hz, 2H),
3.10 (q, J = 7.0 Hz, 2H), 2.25 (s, 3H), 1.45 (t, J = 7.2 Hz, 3H), 1.04 (t, J = 7.1 Hz, 3H);
13
C NMR (100 MHz, CDCl3) δ 146.9, 143.8, 136.3, 133.1, 129.2, 128.8, 127.1, 124.6,
123.4, 122.7, 119.7, 119.6, 117.9, 116.7, 113.0, 110.3, 45.6, 38.0, 21.5, 15.0, 12.8; IR
(neat, cm-1) 3056, 2974, 1595, 1497, 1460, 1377, 1324, 1156, 1091, 738, 689, 662;
HRMS (ESI): calcd for (C25H27N3O2S+H+): 434.1897, Found: 434.1922.

N-(3-(ethyl(phenyl)amino)-1-isopropyl-1H-indol-2-yl)-4-methylbenzenesulfonami
de (7c):
White solid; Yield: 93 mg, 83%; M.p. 165.9-166.8 0C;
1
H NMR (400 MHz, CDCl3) δ 7.61 (d, J = 8.8 Hz, 1H),
7.51 (d, J = 8.3 Hz, 2H), 7.23 – 7.17 (m, 2H), 7.05 –

21 
 
6.95 (m, 5H), 6.63 (t, J = 7.2 Hz, 1H), 6.39 (s, 1H), 6.24 (d, J = 7.9 Hz, 2H), 5.17 –
5.09 (m, 1H), 3.07 (q, J = 7.0 Hz, 2H), 2.26 (s, 3H), 1.69 (d, J = 7.0 Hz, 6H), 1.05 (t,
J = 7.1 Hz, 3H); 13C NMR (100 MHz, CDCl3) δ 146.9, 143.8, 136.2, 131.8, 129.2,
128.8, 127.2, 124.5, 124.0, 122.2, 119.8, 119.2, 117.6, 116.7, 113.0, 112.6, 47.1, 45.6,
21.5, 21.4, 12.9; IR (neat, cm-1) 2974, 1596, 1497, 1456, 1321, 1265, 1158, 1092, 739,
686; HRMS (ESI): calcd for (C26H29N3O2S+H+): 448.2053, Found: 448.2039.

N-(1-allyl-3-(ethyl(phenyl)amino)-1H-indol-2-yl)-4-methylbenzenesulfonamide
(7d):
White solid; Yield: 92 mg, 83%; M.p. 154.9-155.4 0C; 1H
NMR (400 MHz, CDCl3) δ 7.52 (d, J = 8.0 Hz, 2H), 7.36
(d, J = 8.3 Hz, 1H), 7.27 – 7.15 (m, 2H), 7.07 – 6.92 (m,
5H), 6.63 (t, J = 7.2 Hz, 1H), 6.49 (s, 1H), 6.27 (d, J =
8.4 Hz, 2H), 6.02 (m, 1H), 5.19 (d, J = 10.3 Hz, 1H), 5.02
(d, J = 17.2 Hz, 1H), 4.94 (d, J = 4.8Hz, 2H), 3.13 (q, J = 6.5 Hz, 2H), 2.25 (s, 3H),
1.05 (t, J = 7.0 Hz, 3H). 13C NMR (100 MHz, CDCl3) δ 146.9, 143.8, 136.2, 133.9,
133.7, 129.2, 128.8, 127.2, 124.8, 123.3, 122.9, 119.8, 119.7, 118.3, 116.8, 116.6,
113.1, 110.7, 45.6, 45.6, 21.5, 12.9; IR (neat, cm-1) 3058, 2972, 1595, 1497, 1461,
1377, 1326, 1158, 1092, 739, 688, 662; HRMS (ESI): calcd for (C26H27N3O2S+H+):
446.1897, Found: 446.1876.

N-(1-benzyl-3-(ethyl(phenyl)amino)-1H-indol-2-yl)-4-methylbenzenesulfonamide
(7e):
White solid; Yield: 106 mg, 86%; M.p. 156.1-156.9 0C;
N Ph 1
H NMR (400 MHz, CDCl3) δ 7.49 (d, J = 8.0 Hz, 2H),
NH 7.32 – 7.14 (m, 6H), 7.08 – 6.94 (m, 7H), 6.64 (t, J = 7.2
N S
O Hz, 1H), 6.30 (d, J = 7.9 Hz, 2H), 6.20 (s, 1H), 5.54 (s,
Bn O

2H), 3.14 (q, J = 7.1 Hz, 2H), 2.26 (s, 3H), 1.07 (t, J = 7.1 Hz, 3H); 13C NMR (100
MHz, CDCl3) δ 146.9, 143.8, 137.6, 136.3, 133.9, 129.2, 128.8, 128.7, 127.3, 127.2,

22 
 
126.4, 125.1, 123.4, 123.1, 119.9, 119.7, 118.9, 116.9, 113.2, 110.8, 46.6, 45.6, 21.5,
13.0; IR (neat, cm-1) 3033, 2926, 1596, 1496, 1460, 1378, 1328, 1159, 1092, 743, 694;
HRMS (ESI): calcd for (C30H29N3O2S+H+): 496.2053, Found: 496.2021.

N-(3-(ethyl(phenyl)amino)-1H-indol-2-yl)-4-methylbenzenesulfonamide (7f):
White solid; Yield: 89 mg, 88%; M.p. 98.1-99.0 0C; 1H
N Ph
NMR (400 MHz, CDCl3) δ 8.96 (s, 1H), 7.58 (d, J = 8.3
NH
N S
Hz, 2H), 7.39 (d, J = 8.1 Hz, 1H), 7.19 – 7.10 (m, 4H),
O
H O
7.03 – 6.93 (m, 3H), 6.87 (s, 1H), 6.64 (t, J = 7.3 Hz, 1H),
6.35 (d, J = 8.0 Hz, 2H), 3.29 (q, J = 7.1 Hz, 2H), 2.36 (s, 3H), 0.89 (t, J = 7.1 Hz,
13
3H); C NMR (100 MHz,CDCl3) δ 148.1, 144.6, 135.4, 131.8, 130.0, 129.0, 128.2,
127.0, 124.3, 121.9, 120.3, 118.1, 117.4, 113.0, 111.3, 109.3, 45.9, 21.5, 13.0; IR (neat,
cm-1) 2926, 1737, 1615, 1496, 1464, 1328, 1159, 1066, 778, 738, 668; HRMS (ESI):
calcd for (C23H23N3O2S+H+): 406.1584, Found: 406.1570.

N-(3-(ethyl(phenyl)amino)-1,7-dimethyl-1H-indol-2-yl)-4-methylbenzenesulfona
mide (7g):
White solid; Yield: 90 mg, 83%; M.p. 173.1-173.5 0C;
1
H NMR (400 MHz, CDCl3) δ 7.52 (d, J = 8.3 Hz, 2H),
7.03 – 6.92 (m, 6H), 6.90 – 6.82 (m, 1H), 6.61 (t, J = 7.2
Hz, 1H), 6.52 (s, 1H), 6.24 (d, J = 7.9 Hz, 2H), 4.05 (s, 3H), 3.10 (q, J = 7.0 Hz, 2H),
2.80 (s, 3H), 2.25 (s, 3H), 1.03 (t, J = 7.1 Hz, 3H); 13C NMR (100 MHz, CDCl3)
δ147.0, 143.9, 136.2, 133.4, 129.2, 128.8, 127.2, 125.9, 125.6, 124.1, 121.9, 119.7,
117.6, 117.4, 116.7, 113.0, 45.7, 33.1, 21.5, 20.2, 12.9; IR (neat, cm-1) 2969, 1596,
1497, 1453, 1372, 1323, 1158, 1091, 746 , 664; HRMS (ESI): calcd for
(C25H27N3O2S+H+): 434.1897, Found: 434.1879.

N-(7-bromo-3-(ethyl(phenyl)amino)-1-methyl-1H-indol-2-yl)-4-methylbenzenesul
fonamide (7h):

23 
 
 White solid; Yield: 107 mg, 86%; M.p. 157.6-158.3 0C;
1
H NMR (400 MHz, CDCl3) δ 7.54 (d, J = 8.3 Hz, 2H),
7.38 (d, J = 7.2 Hz, 1H), 7.09 (d, J = 8.0Hz, 1H), 7.07 –
6.96 (m, 4H), 6.81 (t, J = 7.7 Hz, 1H), 6.65 (t, J = 7.2
Hz, 1H), 6.44 (s, 1H), 6.25 (d, J = 8.4 Hz, 2H), 4.16 (s,
3H), 3.13 (q, J = 7.0 Hz, 2H), 2.27 (s, 3H), 1.04 (t, J = 7.1 Hz, 3H); 13C NMR (100
MHz, CDCl3) δ 146.8, 144.1, 136.2, 131.1, 129.4, 128.9, 128.1, 127.4, 127.2, 126.5,
120.8, 118.7, 117.8, 117.1, 113.1, 104.6, 45.8, 33.1, 21.6, 13.0; IR (neat, cm-1) 2924,
1595, 1497, 1373, 1325, 1264, 1092, 747, 700, 662; HRMS (ESI): calcd for
(C24H24BrN3O2S+H+): 498.0845, Found: 498.0844.

N-(3-(ethyl(phenyl)amino)-5-methoxy-1-methyl-1H-indol-2-yl)-4-methylbenzenes
ulfonamide(7i):
White solid; Yield: 99 mg, 88%; M.p. 79.6-80.1 0C;
1
N Ph H NMR (400 MHz, CDCl3) δ 7.51 (d, J = 8.3 Hz,
H3CO
NH 2H), 7.25 (d, J = 8.9 Hz, 1H), 7.01 (m, 4H), 6.91
N S
O
O
(dd, J = 8.9, 2.5 Hz, 1H), 6.62 (m, 2H), 6.46 (s, 1H),
6.27 (d, J = 7.9 Hz, 2H), 3.79 (s, 3H), 3.68 (s, 3H), 3.09 (q, J = 7.0 Hz, 2H), 2.27 (s,
3H), 1.05 (t, J = 7.1 Hz, 3H); 13C NMR (100 MHz, CDCl3) δ 154.1, 147.0, 143.9,
136.2, 129.4, 129.3, 128.9, 127.2, 125.8, 123.5, 117.2, 116.7, 113.0, 112.9, 110.9,
101.0, 55.8, 45.7, 30.1, 21.5, 13.1; IR (neat, cm-1) 2929, 1596, 1494, 1380, 1262, 1159,
1092, 751, 695, 663; HRMS (ESI): calcd for (C25H27N3O3S+H+): 450.1846, Found:
450.1886.

N-(5-bromo-3-(ethyl(phenyl)amino)-1-methyl-1H-indol-2-yl)-4-methylbenzenesul
fonamide (7j):
White solid; Yield: 102 mg, 82%; M.p. 151.7-152.4
0
N Ph
C; 1H NMR (400 MHz, CDCl3) δ 7.50 (d, J = 8.3
Br
Hz, 2H), 7.38 – 7.30 (m, 2H), 7.26 – 7.20 (m, 1H),
NH
N S
O 24 
O
 
7.02 (m, 4H), 6.65 (t, J = 7.3 Hz, 1H), 6.49 (s, 1H), 6.24 (d, J = 7.6 Hz, 2H), 3.81 (s,
3H), 3.08 (q, J = 7.1 Hz, 2H), 2.27 (s, 3H), 1.04 (t, J = 7.1 Hz, 3H); 13C NMR (100
MHz, CDCl3) δ 146.8, 144.1, 136.1, 132.7, 129.4, 129.0, 127.2, 126.7, 125.8, 124.8,
121.6, 117.2, 117.0, 113.3, 113.0, 111.6, 45.7, 30.2, 21.5, 13.1; IR (neat, cm-1) 2972,
1596, 1497, 1470, 1376, 1327, 1269, 1158, 1092, 750, 694; HRMS (ESI): calcd for
(C24H24BrN3O2S+H+): 498.0845, Found: 498.0893.
N-(5-chloro-3-(ethyl(phenyl)amino)-1-methyl-1H-indol-2-yl)-4-methylbenzenesul
fonamide (7k):
White solid; Yield: 104 mg, 92%; M.p. 82.5-83.3 0C;
1
N Ph H NMR (400 MHz, CDCl3) δ 7.51 (d, J = 8.0 Hz,
Cl
2H), 7.28 (d, J = 8.4 Hz, 1H), 7.22 – 7.14 (m, 2H),
NH
N S
O 7.02 (m, 4H), 6.66 (t, J = 7.2 Hz, 1H), 6.43 (s, 1H),
O
6.25 (d, J = 8.1 Hz, 2H), 3.82 (s, 3H), 3.07 (q, J =
13
7.0 Hz, 2H), 2.28 (s, 3H), 1.04 (t, J = 7.1 Hz, 3H); C NMR (100 MHz, CDCl3) δ
146.8, 144.1, 136.1, 132.4, 129.4, 129.0, 127.2, 126.8, 125.7, 124.1, 123.2, 118.6,
117.2, 117.1,113.0, 111.2, 45.7, 30.3, 21.6, 13.1; IR (neat, cm-1) 2926, 1597, 1497,
1473, 1328, 1270, 1158, 1092, 750, 694, 661; HRMS (ESI): calcd for
(C24H24ClN3O2S+H+): 454.1351, Found: 454.1398.

N-(3-(ethyl(phenyl)amino)-1-methyl-1H-indol-2-yl)benzenesulfonamide (7l):
White solid; Yield: 99 mg, 98%; M.p. 168.8-169.5 0C; 1H
NMR (400 MHz, CDCl3) δ 7.63 (dd, J = 8.0, 0.8 Hz, 2H),
7.38 (m, 2H), 7.30 – 7.23 (m, 4H), 7.07 – 7.01 (m, 3H), 6.65
(t, J = 7.3 Hz, 1H), 6.36 (s, 1H), 6.28 (d, J = 7.6 Hz, 2H),
3.83 (s, 3H), 2.99 (q, J = 7.1 Hz, 2H), 1.04 (t, J = 7.1 Hz, 3H); 13C NMR (100 MHz,
CDCl3) δ 146.9, 139.2, 134.1, 132.9, 129.1, 128.7, 127.3, 124.9, 123.1, 122.9, 119.8,
119.4, 117.9, 117.0, 113.1, 110.0, 45.5, 30.0, 13.0; IR (neat, cm-1) 2926, 1594, 1496,
1469, 1327, 1265, 1160, 1092, 750, 688; HRMS (ESI): calcd for (C23H23N3O2S+H+):
406.1584, Found: 406.1623.

25 
 
4-methyl-N-(1-methyl-3-(methyl(phenyl)amino)-1H-indol-2-yl)benzenesulfonami
de (7m):
White solid; Yield: 92 mg, 91%; M.p. 159.2-159.9 0C; 1H
NMR (400 MHz, CDCl3) δ 7.47 (d, J = 8.3 Hz, 2H), 7.37
(d, J = 8.5 Hz, 1H), 7.31 – 7.25 (m, 2H), 7.18 – 7.08 (m,
4H), 7.05 (t, J = 7.5 Hz, 1H), 6.69 (t, J = 7.3 Hz, 1H),
13
6.31 (d, J = 8.0 Hz, 2H), 6.11 (s, 1H), 3.85 (s, 3H), 2.58 (s, 3H), 2.36 (s, 3H); C
NMR (100 MHz, CDCl3) δ 147.9, 143.9, 136.2, 134.2, 129.4, 129.4, 127.6, 124.5,
122.9, 122.1, 119.7, 119.0, 118.0, 117.3, 112.1, 110.1, 38.3, 29.9, 21.5; IR (neat, cm-1)
2924, 1595, 1498, 1470, 1375, 1330, 1262, 1158, 1091, 748, 690, 662; HRMS (ESI):
calcd for (C23H23N3O2S+H+): 406.1584, Found:406.1663.

N-(3-(isopropyl(phenyl)amino)-1-methyl-1H-indol-2-yl)-4-methylbenzenesulfona
mide (7n):
White solid; Yield: 77 mg, 71%; M.p. 150.2-151.0 0C;
1
H NMR (400 MHz, CDCl3) δ 7.48 (d, J = 8.3 Hz, 2H),
7.36 (d, J = 8.0 Hz, 1H), 7.27 – 7.21 (m, 1H), 7.13 (d, J
= 7.9 Hz, 1H), 7.02 – 6.84 (m, 5H), 6.60 (t, J = 7.2 Hz,
1H), 6.53 (s, 1H), 6.27 (d, J = 8.1 Hz, 2H), 4.02 (m, 1H), 3.86 (s, 3H), 2.23 (s, 3H),
1.05 (d, J = 6.5 Hz, 6H); 13C NMR (100 MHz, CDCl3) δ 148.2, 143.7, 136.4, 134.3,
129.1, 128.5, 128.1, 127.0, 124.6, 122.7, 120.4, 119.8, 116.7, 113.9, 113.5, 109.9, 49.5,
30.3, 21.5, 21.1; IR (neat, cm-1) 2926, 1595, 1495, 1377, 1326, 1275, 1159, 1093, 751;
HRMS (ESI): calcd for (C25H27N3O2S+H+): 434.1897, Found:434.1914.

N-(3-(benzyl(phenyl)amino)-1-methyl-1H-indol-2-yl)-4-methylbenzenesulfonami
de (7o):

Bn White solid; Yield: 110 mg, 89%; M.p. 193.3-194.2 0C;

N Ph 1
H NMR (400 MHz, CDCl3) δ 7.46 (d, J = 8.3 Hz, 2H),
NH
N S 26 
O
  O
7.37 (d, J = 8.3 Hz, 1H), 7.31 – 7.20 (m, 5H), 7.12 – 7.07 (m, 2H), 7.02 (m, 5H), 6.69
(t, J = 7.3 Hz, 1H), 6.37 (d, J = 8.0 Hz, 2H), 5.71 (s, 1H), 4.20 (s, 2H), 3.79 (s, 3H),
2.32 (s, 3H); 13C NMR (100 MHz, CDCl3) δ 147.7, 144.0, 139.0, 136.1, 134.3, 129.4,
129.0, 128.7, 127.5, 127.2, 127.0, 125.6, 122.9, 122.4, 119.8, 119.2, 117.8, 117.7,
113.8, 110.1, 55.9, 30.0, 21.6; IR (neat, cm-1) 2924, 1594, 1495, 1379, 1322, 1259,
1156, 1093, 748, 698, 662; HRMS (ESI): calcd for (C29H27N3O2S+H+): 482.1897,
Found: 482.1903.

N-(3-(diphenylamino)-1-methyl-1H-indol-2-yl)-4-methylbenzenesulfonamide
(7p):

Ph White solid; Yield: 108 mg, 90%; M.p. 194.9-195.5 0C;

N Ph 1
H NMR (400 MHz, CDCl3) δ 7.56 (d, J = 8.0 Hz, 2H),
NH
N S 7.35 (d, J = 8.3 Hz, 1H), 7.24 ( m, 1H), 7.14 – 7.07 (m,
O
O
4H), 7.04 (d, J = 8.0 Hz, 2H), 6.94 – 6.82 (m, 4H), 6.63
(d, J = 7.6 Hz, 4H), 5.47 (s, 1H), 3.83 (s, 3H), 2.20 (s, 3H); 13C NMR (100 MHz,
CDCl3) δ 145.3, 144.3, 135.9, 134.3, 129.5, 128.9, 127.7, 124.0, 122.9, 121.6, 120.37,
119.8, 119.6, 117.0, 110.0, 29.9, 21.5; IR (neat, cm-1) 2924, 1588, 1489, 1373, 1334,
1261, 1161, 1091, 747, 696, 661; HRMS (ESI): calcd for (C28H25N3O2S+H+):
468.1740, Found: 468.1751.

N-(3-(benzyl(phenyl)amino)-1-ethyl-1H-indol-2-yl)-4-methylbenzenesulfonamide
(7q):
White solid; Yield: 101 mg, 82%; M.p. 165.3-166.2 0C;
1
H NMR (400 MHz, CDCl3) δ 7.45 (d, J = 8.3 Hz, 2H),
7.40 (d, J = 8.3 Hz, 1H), 7.31 – 7.18 (m, 5H), 7.10 – 6.96
(m, 7H), 6.69 (t, J = 7.3 Hz, 1H), 6.36 (d, J = 7.6 Hz, 2H),
5.62 (s, 1H), 4.34 (q, J = 7.2 Hz, 2H), 4.21 (s, 2H), 2.29 (s, 3H), 1.35 (t, J = 7.2 Hz,
3H); 13C NMR (100 MHz, CDCl3) δ 147.7, 143.9, 138.8, 136.0, 133.2 , 129.3, 128.9,
128.6, 127.4, 127.3, 127.3, 125.1, 122.8, 122.6, 119.7, 119.4, 117.7, 117.7, 113.8,

27 
 
110.5, 55.6, 38.0, 21.6, 14.8; IR (neat, cm-1) 2926, 1596, 1496, 1458, 1376, 1339,
1159, 1091, 742, 698, 663; HRMS (ESI): calcd for (C30H29N3O2S+H+): 496.2053,
Found: 496.2029.

N-(1-allyl-3-(benzyl(phenyl)amino)-1H-indol-2-yl)-4-methylbenzenesulfonamide
(7r):
White solid; Yield: 100 mg, 79%; M.p. 147.5-148.1 0C;
1
H NMR (400 MHz, CDCl3) δ 7.46 (d, J = 8.0 Hz, 2H),
7.36 (d, J = 8.0 Hz, 1H), 7.30 – 7.19 (m, 5H), 7.09 (d, J =
6.5 Hz, 2H), 7.06 – 6.96 (m, 5H), 6.70 (t, J = 7.2 Hz, 1H),
6.38 (d, J = 8.4 Hz, 2H), 5.93 (m, 1H), 5.63 (s, 1H), 5.14
(d, J = 10.4 Hz, 1H), 4.96 – 4.84 (m, 3H), 4.23 (s, 2H), 2.30 (s, 3H); 13C NMR (100
MHz, CDCl3) δ 147.6, 143.9, 138.8, 136.0, 133.9, 133.7, 129.4, 128.9, 128.6, 127.5,
127.2, 125.0, 123.0 , 122.6, 119.9, 119.4, 118.3, 117.8, 116.5, 113.9, 110.9, 55.6, 45.6,
21.6; IR (neat, cm-1) 3059, 2923, 1596, 1497, 1460, 1375, 1325, 1159, 1023, 738, 696;
HRMS (ESI): calcd for (C31H29N3O2S+H+): 508.2053, Found: 506.2039.

N-(3-(benzyl(phenyl)amino)-1H-indol-2-yl)-4-methylbenzenesulfonamide (7s):
White solid; Yield: 95 mg, 81%; M.p. 148.9-149.4 0C; 1H
NMR (400 MHz, CDCl3) δ 8.80 (s, 1H), 7.43 (d, J = 8.3
Hz, 2H), 7.36 (d, J = 8.1 Hz, 1H), 7.32 – 7.25 (m, 3H),
7.16 (m, 4H), 7.05 – 6.93 (m, 5H), 6.67 (t, J = 7.3 Hz,
1H), 6.52 (s, 1H), 6.39 (d, J = 8.0 Hz, 2H), 4.44 (s, 2H), 2.31 (s, 3H); 13C NMR (100
MHz, CDCl3) δ 148.4, 144.4, 139.2, 135.2, 131.9, 129.8, 129.0, 128.8, 127.6, 127.3,
126.8, 126.8, 123.6, 122.2, 120.3, 118.2, 117.9, 113.4, 111.4, 111.3, 56.1, 21.5; IR
(neat, cm-1) 2923, 1595, 1495, 1457, 1354, 1159, 1088, 740, 696, 669; HRMS (ESI):
calcd for (C28H25N3O2S+H+): 468.1740, Found: 468.1718.

N-(3-(benzyl(phenyl)amino)-1-methyl-1H-indol-2-yl)benzenesulfonamide (7t):

28 
 
 White solid; Yield: 100 mg, 86%; M.p. 180.0-181.0 0C; 1H
NMR (400 MHz, CDCl3) δ 7.58 (d, J = 7.3 Hz, 2H), 7.45 (t,
J = 7.5 Hz, 1H), 7.37 (d, J = 8.3 Hz, 1H), 7.33 – 7.20 (m,
7H), 7.04 (m, 5H), 6.70 (t, J = 7.3 Hz, 1H), 6.37 (d, J = 8.0
Hz, 2H), 5.75 (s, 1H), 4.14 (s, 2H), 3.79 (s, 3H); 13C NMR (100 MHz, CDCl3) δ 147.5,
139.1, 138.9, 134.2, 133.0, 129.1, 128.8, 128.6, 127.5, 127.1, 126.9, 125.0, 123.0,
122.3, 119.8, 119.2, 118.1, 117.8, 113.8, 110.1, 55.6, 30.0; IR (neat, cm-1) 2925, 1592,
1496, 1447, 1380, 1322, 1158, 1091, 746, 685; HRMS (ESI): calcd for
(C28H25N3O2S+H+): 468.1740, Found: 468.1707.

4-methyl-1,2-diphenyl-1,4-dihydroimidazo[4,5-b]indole (8a):
yellow solid; Yield: 25 mg, 31%; M.p. 141.6-142.3 0C; 1H
NMR (400 MHz, CDCl3) δ 7.57 – 7.41 (m, 7H), 7.38 ( m,
2H), 7.32 – 7.26 (m, 3H), 7.26 – 7.20 (m, 1H), 7.04 (m,
13
1H), 3.96 (s, 3H); C NMR (100 MHz, CDCl3) δ 148.1,
147.7, 139.8, 138.5, 130.9, 129.6, 128.9, 128.3, 128.2,
127.9, 126.1, 121.3, 118.6, 117.0, 116.5, 113.9, 109.7, 29.2; IR (neat, cm-1) 2922,
1598, 1544, 1494, 1468, 1402, 1318, 1267, 1021, 735, 696; HRMS (EI): calcd for
C22H17N3: 323.1422, Found: 323.1426.

4-ethyl-1,2-diphenyl-1,4-dihydroimidazo[4,5-b]indole (8b):
yellow solid; Yield: 30 mg, 36%; M.p. 153.4-154.2 0C; 1H
NMR (400 MHz, CDCl3) δ 7.56 – 7.40 (m, 8H), 7.38 (d, J
= 7.9 Hz, 1H), 7.32 – 7.26 (m, 3H), 7.22 (t, J = 7.7 Hz, 1H),
7.03 (t, J = 7.5 Hz, 1H), 4.46 (q, J = 7.2 Hz, 2H), 1.56 (t, J
= 7.2 Hz, 3H); 13C NMR (100 MHz, CDCl3) δ 147.7, 147.5,
138.7, 138.5, 131.0, 129.6, 129.0, 128.3, 128.2, 127.9, 126.1, 121.2, 118.4,
117.2, 116.6, 114.0, 109.8 , 38.0, 14.9; IR (neat, cm-1) 3058, 2973, 1599, 1534, 1494,

29 
 
1458, 1405, 1378, 1341, 1313, 735, 695; HRMS (EI): calcd for C23H19N3: 337.1579,
Found: 337.1585.

4-allyl-1,2-diphenyl-1,4-dihydroimidazo[4,5-b]indole (8c):
yellow solid; Yield: 29 mg, 33%; M.p. 120.2-121.0 0C; 1H
NMR (400 MHz, CDCl3) δ 7.54 – 7.43 (m, 7H), 7.40 –
7.36 (m, 2H), 7.29 (m, 3H), 7.23 – 7.18 (m, 1H), 7.07 –
7.02 (m, 1H), 6.16 – 6.05 (m, 1H), 5.23 (t, J = 1.5 Hz,
1H), 5.20 (dd, J = 6.8, 1.3 Hz, 1H), 5.02 (dt, J = 5.2, 1.2
Hz, 2H); 13C NMR (100 MHz, CDCl3) δ 147.7, 147.7,
139.2, 138.5, 133.2 , 130.9, 129.6, 129.0, 128.3, 128.0, 126.1, 121.4, 118.8, 117.1,
116.8, 116.6, 114.2, 110.5, 45.6; IR (neat, cm-1) 3060, 2923, 1601, 1536, 1496, 1464,
1405, 1319, 1339, 920, 737, 700; HRMS (EI): calcd for C24H19N3: 349.1579, Found:
349.1573.

30 
 
Copies of 1H & 13C NMR Spectra

1
H NMR Spectrum for 3a (CDCl3, 400 MHz)

13
C NMR Spectrum for 3a (CDCl3, 400 MHz)

31 
 
 1
H NMR Spectrum for 3b (CDCl3, 400 MHz)

13
C NMR Spectrum for 3b (CDCl3, 400 MHz)

32 
 
 1
H NMR Spectrum for 3c (CDCl3, 400 MHz)

13
C NMR Spectrum for 3c (CDCl3, 400 MHz)

33 
 
 1
H NMR Spectrum for 3d (CDCl3, 400 MHz) 

13
C NMR Spectrum for 3d (CDCl3, 400 MHz)

34 
 
 1
H HMR Spectrum for 3e (CDCl3, 400 MHz)

13
C NMR Spectrum for 3e (CDCl3, 400 MHz)

35 
 
 1
H NMR Spectrum for 3f (CDCl3, 400 MHz)

13
C NMR Spectrum for 3f (CDCl3, 400 MHz)

36 
 
 1
H NMR Spectrum for 3g (CDCl3, 400 MHz)

13
C NMR Spectrum for 3g (CDCl3, 400 MHz)

37 
 
 1
H NMR Spectrum for 3h (CDCl3, 400 MHz)

13
C NMR Spectrum for 3h (CDCl3, 400 MHz)

38 
 
 1
H NMR Spectrum for 3i (CDCl3, 400 MHz)

13
C NMR Spectrum for 3i (CDCl3, 400 MHz)

39 
 
 1
H NMR Spectrum for 3j (CDCl3, 400 MHz)

13
C NMR Spectrum for 3j (CDCl3, 400 MHz)

40 
 
 1
H NMR Spectrum for 3k (CDCl3, 400 MHz)

13
C NMR Spectrum for 3k (CDCl3, 400 MHz)

41 
 
 1
H NMR Spectrum for 3l (CDCl3, 400 MHz)
129.560
155.645

140.334
142.335

132.545

126.262
122.864

32.305
119.409
129.319

77.000
76.682
121.703

114.765

19.569
21.469
77.318

-
N
+
N
CH3

N
N S
O
CH3 O
CH3

140 135 130 125 120 115

f1 (ppm)

190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0
f1 (ppm)
13
C NMR Spectrum for 3l (CDCl3, 400 MHz)

42 
 
 1
H NMR Spectrum for 3m (CDCl3, 400 MHz)

13
C NMR Spectrum for 3m (CDCl3, 400 MHz)

43 
 
 1
H NMR Spectrum for 3n (CDCl3, 400 MHz)

13
C NMR Spectrum for 3n (CDCl3, 400 MHz)

44 
 
 1
H NMR Spectrum for 3o (CDCl3, 400 MHz)

13
C NMR Spectrum for 3o (CDCl3, 400 MHz)

45 
 
 1
H NMR Spectrum for 3p (CDCl3, 400 MHz)

13
C NMR Spectrum for 3p (CDCl3, 400 MHz)

46 
 
 

1
H NMR Spectrum for 3q (DMSO-d6, 400 MHz) 

13
C NMR Spectrum for 3q (DMSO-d6, 400 MHz)

47 
 
 1
H NMR Spectrum for 4a (CDCl3, 400 MHz)

13
C NMR Spectrum for 4a (CDCl3, 400 MHz)

48 
 
 1
H NMR Spectrum for 4b (CDCl3, 400 MHz)

13
C NMR Spectrum for 4b (CDCl3, 400 MHz)

49 
 
 1
H NMR Spectrum for 4c' (DMSO-D6, 400 MHz)

13
C NMR Spectrum for 4c' (DMSO-D6, 400 MHz)

50 
 
 1
H NMR Spectrum for 4c+4c' (CDCl3, 400 MHz)

13
C NMR Spectrum for 4c+4c' (CDCl3, 400 MHz)

51 
 
 1
H NMR Spectrum for 4d' (DMSO-D6, 400 MHz)

13
C NMR Spectrum for 4d' (DMSO-D6, 400 MHz)

52 
 
 1
H NMR Spectrum for 4d+4d' (CDCl3, 400 MHz)

13
C NMR Spectrum for 4d+4d' (CDCl3, 400 MHz)

53 
 
 1
H NMR Spectrum for 4e (CDCl3, 400 MHz)

13
C NMR Spectrum for 4e (CDCl3, 400 MHz)

54 
 
 1
H NMR Spectrum for 4e' (DMSO-D6, 400 MHz)

13
C NMR Spectrum for 4e' (DMSO-D6, 400 MHz)

55 
 
 1
H NMR Spectrum for 4f' (DMSO-D6, 400 MHz)

13
C NMR Spectrum for 4f' (DMSO-D6, 400 MHz)

56 
 
 1
H NMR Spectrum for 4f+4f' (CDCl3, 400 MHz)

13
C NMR Spectrum for 4f+4f' (CDCl3, 400 MHz)

57 
 
 1
H NMR Spectrum for 4g (CDCl3, 400 MHz)

13
C NMR Spectrum for 4g (CDCl3, 400 MHz)

58 
 
 1
H NMR Spectrum for 4g' (DMSO-D6, 400 MHz)

13
C NMR Spectrum for 4g' (DMSO-D6, 400 MHz)

59 
 
 1
H NMR Spectrum for 4h (CDCl3, 400 MHz)

13
C NMR Spectrum for 4h (CDCl3, 400 MHz)

60 
 
 1
H NMR Spectrum for 4h' (DMSO-D6, 400 MHz)

13
C NMR Spectrum for 4h' (DMSO-D6, 400 MHz)

61 
 
 1
H NMR Spectrum for 4i' (DMSO-D6, 400 MHz)

13
C NMR Spectrum for 4i' (DMSO-D6, 400 MHz)

62 
 
 1
H NMR Spectrum for 4i+4i' (CDCl3, 400 MHz)

13
C NMR Spectrum for 4i+4i' (CDCl3, 400 MHz)

63 
 
 1
H NMR Spectrum for 5a (DMSO-D6, 400 MHz)

13
C NMR Spectrum for 5a (DMSO-D6, 400 MHz)

64 
 
 1
H NMR Spectrum for 5b (CDCl3, 400 MHz)

13
C NMR Spectrum for 5b (CDCl3, 400 MHz)

65 
 
 1
H NMR Spectrum for 5c (CDCl3, 400 MHz)

13
C NMR Spectrum for 5c (CDCl3, 400 MHz)

66 
 
 1
H NMR Spectrum for 5d (CDCl3, 400 MHz)

13
C NMR Spectrum for 5d (CDCl3, 400 MHz)

67 
 
 1
H NMR Spectrum for 5e (DMSO-D6, 400 MHz)

13
C NMR Spectrum for 5e (DMSO-D6, 400 MHz)

68 
 
 1
H NMR Spectrum for 5f (CDCl3, 400 MHz)

13
C NMR Spectrum for 5f (CDCl3, 400 MHz)

69 
 
 1
H NMR Spectrum for 5g (CDCl3, 400 MHz)

13
C NMR Spectrum for 5g (CDCl3, 400 MHz)

70 
 
 1
H NMR Spectrum for 5h (CDCl3, 400 MHz)

13
C NMR Spectrum for 5h (CDCl3, 400 MHz)

71 
 
 1
H NMR Spectrum for 5i (CDCl3, 400 MHz)

13
C NMR Spectrum for 5i (CDCl3, 400 MHz)

72 
 
 1
H NMR Spectrum for 5j (CDCl3, 400 MHz)

13
C NMR Spectrum for 5j (CDCl3, 400 MHz)

73 
 
 1
H NMR Spectrum for 7a (CDCl3, 400 MHz)

13
C NMR Spectrum for 7a (CDCl3, 400 MHz)

74 
 
 1
H NMR Spectrum for 7b (CDCl3, 400 MHz)

13
C NMR Spectrum for 7b (CDCl3, 400 MHz)

75 
 
 1
H NMR Spectrum for 7c (CDCl3, 400 MHz)

13
C NMR Spectrum for 7c (CDCl3, 400 MHz)

76 
 
 1
H NMR Spectrum for 7d (CDCl3, 400 MHz)

13
C NMR Spectrum for 7d (CDCl3, 400 MHz)

77 
 
 1
H NMR Spectrum for 7e (CDCl3, 400 MHz)

13
C NMR Spectrum for 7e (CDCl3, 400 MHz)

78 
 
 1
H NMR Spectrum for 7f (CDCl3, 400 MHz)

13
C NMR Spectrum for 7f (CDCl3, 400 MHz)

79 
 
 1
H NMR Spectrum for 7g (CDCl3, 400 MHz)

13
C NMR Spectrum for 7g (CDCl3, 400 MHz) 

80 
 
 1
H NMR Spectrum for 7h (CDCl3, 400 MHz)

13
C NMR Spectrum for 7h (CDCl3, 400 MHz)

81 
 
 1
H NMR Spectrum for 7i (CDCl3, 400 MHz)

13
C NMR Spectrum for 7i (CDCl3, 400 MHz)

82 
 
 1
H NMR Spectrum for 7j (CDCl3, 400 MHz)

13
C NMR Spectrum for 7j (CDCl3, 400 MHz)

83 
 
 1
H NMR Spectrum for 7k (CDCl3, 400 MHz)

13
C NMR Spectrum for 7k (CDCl3, 400 MHz)

84 
 
 1
H NMR Spectrum for 7l (CDCl3, 400 MHz)

13
C NMR Spectrum for 7l (CDCl3, 400 MHz)

85 
 
 1
H NMR Spectrum for 7m (CDCl3, 400 MHz)

13
C NMR Spectrum for 7m (CDCl3, 400 MHz)

86 
 
 1
H NMR Spectrum for 7n (CDCl3, 400 MHz)

13
C NMR Spectrum for 7n (CDCl3, 400 MHz)

87 
 
 1
H NMR Spectrum for 7o (CDCl3, 400 MHz)

13
C NMR Spectrum for 7o (CDCl3, 400 MHz)

88 
 
 1
H NMR Spectrum for 7p (CDCl3, 400 MHz)
135.908

109.985
128.937
134.260
145.322
144.273

29.923
76.683
116.976
119.807

77.000
121.615

77.318

21.451

N
CH3

NH
N S
O
CH3 O

144 138 132 126 120 114

f1 (ppm)

190 170 160 140 130 110 90 80 70 60 50 40 30 20 10 0

f1 (ppm)  
13
C NMR Spectrum for 7p (CDCl3, 400 MHz)

89 
 
 1
H NMR Spectrum for 7q (CDCl3, 400 MHz)

13
C NMR Spectrum for 7q (CDCl3, 400 MHz)

90 
 
 1
H NMR Spectrum for 7r (CDCl3, 400 MHz) 

13
C NMR Spectrum for 7r (CDCl3, 400 MHz)

91 
 
 1
H NMR Spectrum for 7s (CDCl3, 400 MHz)

13
C NMR Spectrum for 7s (CDCl3, 400 MHz)

92 
 
 1
H NMR Spectrum for 7t (CDCl3, 400 MHz)
138.865
139.057
147.499

55.566
122.316

29.946
129.120

113.806
110.089
133.014

76.682
77.000
117.821

77.317

NH
N S

137 127
O
CH3 O

f1 (ppm)

190 170 160 140 120 110 90 80 70 60 50 40 30 20 10 0

f1 (ppm)  
13
C NMR Spectrum for 7t (CDCl3, 400 MHz)

93 
 
 1
H NMR Spectrum for 8a (CDCl3, 400 MHz)

13
C NMR Spectrum for 8a (CDCl3, 400 MHz)

94 
 
 0.000
7.050

0.074
4.428
7.430

7.409

7.286
7.458

4.482
4.464
4.446
7.387
7.367
7.440

7.294

7.278
7.454

7.237

1.559
7.031
7.199
7.218
7.251

7.012
7.416

1.577

1.541
1.715
N

N
N

CH3

7.55 7.45 7.35 7.25 7.15 7.05

f1 (ppm)

2.00

3.00
0.99
7.97

1.00
3.01
1.01

9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0
f1 (ppm)  
1
H NMR Spectrum for 8b (CDCl3, 400 MHz) 

13
C NMR Spectrum for 8b (CDCl3, 400 MHz)

95 
 
 1
H NMR Spectrum for 8c (CDCl3, 400 MHz)

13
C NMR Spectrum for 8c (CDCl3, 400 MHz)

96 
 
Crystal Structures of 3a, 3l and 4g

1. Compound 3d

2. Compound 3l

97 
 
3. Compound 4g

98