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Characterization Data for Products
3-(Phenylthio)-2-methylindole (2a): Colorless prisms, mp 109–110 8C. IR
(KBr): vmax cm21 3398.8, 3055.8, 1580.9, 1476.4, 1454.2, 1403.6, 1290.6,
741.9, 692.0. 1H NMR (300 MHz, CDCl3): d 8.17 (s, 1H, NH), 7.53
(d, J ¼ 7.5 Hz, 1H, arom), 7.31 (d, J ¼ 7.5 Hz, 1H, arom), 7.15 (m, 4H,
arom), 7.01 (m, 3H, arom), 2.47 (s, 3H, CH3). 13C NMR (75 MHz, CDCl3):
d 141.1, 139.3, 135.4, 130.2, 128.7, 125.4, 124.5, 122.1, 120.6, 118.9,
110.6, 99.1, 12.1. MS (EI): m/z 239 (Mþ), 223, 162, 130, 118, 77. HR-ESI-
MS: m/z found M þ H ¼ 240.0843, C15H13NS requires M þ H ¼ 240.0841.
3-(Phenylthio)-indole (2b): Colorless prisms, mp 149–151 8C. IR (KBr): vmax
cm21 3402.6, 3050.7, 2198.5, 1574.2, 1472.9, 1068.1, 1015.6, 739.5, 575.4. 1H
NMR (300 MHz, CDCl3): d 8.37 (s, 1H, NH), 7.63 (d, 1H, J ¼ 5.7 Hz, arom),
7.48 (d, 1H, J ¼ 1.8 Hz, arom), 7.44 (d, 1H, J ¼ 6 Hz, arom), 7.29 (d, 1H,
J ¼ 5.4 Hz, arom), 7.26 (d, 1H, J ¼ 2.1 Hz, arom), 7.18 (m, 3H, arom), 7.16
(d, 1H, J ¼ 5.1 Hz, arom), 7.06 (t, 1H, J ¼ 5.1 Hz, J ¼ 6 Hz, arom). 13C
NMR (75 MHz, CDCl3): d 130.6, 129.0, 128.7, 125.8, 124.7, 123.0, 120.9,
119.6, 111.6. MS (EI): m/z 225 (Mþ), 193, 165, 148, 121, 77. HR-ESI-MS:
m/z calcd. for C14H11NS þ H: 226.0685; found: 226.0691.
3-(4-Methoxyl-phenylthio)-2-methylindole (2c): Colorless prisms, mp 119–
120 8C. IR (KBr): nmax cm21 3394.9, 1592.8, 1490.9, 1455.7, 1287.2, 1241.5,
1176.3, 1029.7, 823.7, 746.6. H NMR (300 MHz, CDCl3): d 8.14 (s, 1H,
1
NH), 7.60 (d, 1H, J ¼ 7.5 Hz, arom), 7.32 (d, 1H, J ¼ 1.2 Hz, arom), 7.21
(m, 2H, arom), 7.07 (m, 2H, arom), 6.74 (dd, 2H, J ¼ 2.4 Hz, J ¼ 3.0 Hz,
J ¼ 9.0 Hz, arom), 3.74 (s, 3H, OCH3), 2.51 (s, 3H, CH3). 13C NMR
(75 MHz, CDCl3): d 157.5, 140.6, 135.3, 129.8, 127.8, 122.0, 120.6, 118.9,
114.4, 110.6, 100.8, 55.3, 12.1. MS (EI): m/z 269 (Mþ), 254, 238, 223,
162, 77. Anal. calcd. for C16H15N1S1O1: C, 71.35; H, 5.61; N, 5.20; O,
5.94; S, 11.90. Found: C, 70.97; H, 5.97; N, 5.13; O, 6.06; S, 11.87.
3-(4-Chloro-phenylthio)-2-methylindole (2d): Colorless prisms, mp 106–
107 8C. IR (KBr): nmax cm21 3394.1, 3056.9, 2915.6, 1473.1, 1453.8,
1089.8, 1009.4, 814.8, 745.6. H NMR (300 MHz, CDCl3): d 8.20 (s, 1H,
1
NH), 7.54 (d, 1H, J ¼ 6.9 Hz, arom), 7.35 (d, 1H, J ¼ 7.5 Hz, arom), 7.18
(m, 4H, arom), 6.97 (dd, 2H, J ¼ 1.8 Hz, J ¼ 2.4 Hz, J ¼ 8.7 Hz, arom),
2.51 (s, 3H, CH3). 13C NMR (75 MHz, CDCl3): d 141.2, 137.9, 135.4,
130.2, 129.9, 128.7, 126.7, 122.3, 120.8, 118.8, 110.7, 98.9, 12.1. MS (EI):
m/z 273 (Mþ), 238, 161, 146, 117, 77. Anal. calcd. for C15H12N1S1Cl1: C,
65.81; H, 4.42; N, 5.12; Cl, 12.95; S, 11.71. Found: C, 65.92; H, 4.46; N,
4.69; Cl, 12.85; S, 12.08.
3-(20-Pyridylthio)-2-methylindole (2e): Colorless prisms, mp 159–160 8C.
IR (KBr): vmax cm21 3387.8, 3179.8, 3155.6, 1577.3, 1556.3, 1450.9,