SYNTHESIS OF 1-PHENYLSULFONYL-2-AROYLINDOLES
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removed, and the residue was quenched with ice water (50 mL), extracted with
chloroform (3 ꢀ 10 mL), and dried (Na2SO4). Removal of solvent followed by
crystallization from methanol afforded the 1-phenylsulfonyl-p-chlorophenyl-3-
(hydroxyindolin-2-yl)methanone (0.60 g, 76%). Mp: 208–210 ꢁC. IR (KBr): 3440
1
(OH), 1659 (CO), 1372 & 1179 (SO2Ph) cmꢂ1. H NMR (300 MHz, CDCl3): d
7.97 (d, J ¼ 7.8 Hz, 2H, Ar-H), 7.87 (d, J ¼ 8.1 Hz, 2H, Ar-H), 7.60 (d, J ¼ 6.9 Hz,
1H, Ar-H), 7.52–7.49 (m, 5H, Ar-H), 7.28 (t, J ¼ 7.8 Hz, 2H, Ar-H), 7.04 (t,
J ¼ 7.2 Hz, 1H, Ar-H), 5.92 (s, 1H, OH), 5.70-5.58 (m, 2H, CH). 13C NMR
(75 MHz, CDCl3): d 192.6, 140.8, 138.4, 137.1, 134.9, 133.3, 132.4, 129.8, 129.4,
128.9, 128.8, 128.3, 127.0, 126.8, 125.7, 123.6, 113.5, 71.1, 69.6. Mass (m=z) %:
415 (Mþ þ 2, 30%), 413 (Mþ, 90%). Anal. calcd. for C21H16ClNO4S: C, 60.94; H,
3.90; N, 3.38; S, 7.75%. Found: C, 60.76; H, 3.68; N, 3.20; S, 7.63%.
1-Phenylsulfonyl-(4-chlorophenyl)(1H-indol-2-yl)methanone (3c). Yield:
0.53 g (70%). Mp: 120–122 ꢁC. IR (KBr): 1659 (CO), 1370 & 1174 (SO2Ph) cmꢂ1. 1H
NMR (300 MHz, CDCl3): d 8.13 (d, J ¼ 8.4 Hz, 1H, Ar-H), 8.03–8.01 (m, 2H, Ar-H),
7.91 (d, J ¼ 8.7 Hz, 2H, Ar-H), 7.58–7.55 (m, 2H, Ar-H), 7.50–7.44 (m, 5H, Ar-H),
7.30 (t, J ¼ 6.9 Hz, 1H, Ar-H), 6.94 (s, 1H, Ar-H). 13C NMR (75 MHz, CDCl3): d
186.4, 140.1, 137.9, 137.7, 137.6, 135.9, 134.0, 131.3, 129.0, 128.9, 128.6, 127.5,
127.2, 124.4, 122.6, 116.9, 115.2. Mass (m=z) %: 397 (Mþ þ 2, 30%), 395 (Mþ,
88%). Anal. calcd. for C21H14ClNO3S: C, 63.72; H, 3.56; N, 3.54; S, 8.10%. Found:
C, 63.50; H, 3.40; N, 3.80; S, 8.28%.
1-Phenylsulfonyl-(4-bromophenyl)(1H-indol-2-yl)methanone (3d). Yield:
1
0.62 g (74%). Mp: 146 ꢁC. IR (KBr): 1659 (CO), 1364 & 1170 (SO2Ph) cmꢂ1. H
NMR (300 MHz, CDCl3): d 8.13 (d, J ¼ 8.1 Hz, 1H, Ar-H), 8.01 (d, J ¼ 7.5 Hz,
2H, Ar-H), 7.82 (d, J ¼ 8.1 Hz, 2H, Ar-H), 7.62–7.43 (m, 7H, Ar-H), 7.28
(t, J ¼ 7.2 Hz, 1H, Ar-H), 6.94 (s, 1H, Ar-H). 13C NMR (75 MHz, CDCl3): d
186.5, 137.9, 137.7, 137.5, 136.3, 134.1, 131.9, 131.4, 129.1, 128.8, 128.6, 127.5,
127.3, 124.5, 122.7, 117.1, 115.2. Mass (m=z) %: 441 (Mþ þ 2, 33%), 439 (Mþ,
34%). Anal. calcd. for C21H14BrNO3S: C, 57.28; H, 3.20; N, 3.18; S, 7.28%. Found:
C, 57.50; H, 3.40; N, 3.01; S, 7.46%.
1-Phenylsulfonyl-(1H-indol-2-yl)(4-methoxyphenyl)methanone (3e). Yield:
0.45 g (60%). IR (KBr): 1655 (CO), 1372 & 1173 (SO2Ph) cmꢂ1. 1H NMR (300 MHz,
CDCl3): d 8.13–8.04 (m, 3H, Ar-H), 7.95 (d, J ¼ 9.0 Hz, 2H, Ar-H), 7.53–7.37 (m, 5H,
Ar-H), 7.24 (t, J ¼ 7.5 Hz, 1H, Ar-H), 6.92 (d, J ¼ 9.0 Hz, 2H, Ar-H), 6.86 (s, 1H,
Ar-H), 3.80 (s, 3H, -OCH3). 13C NMR (75 MHz, CDCl3): d 186.3, 164.1, 138.1,
138.0, 137.4, 134.0, 132.5, 130.4, 129.0, 128.8, 127.5, 126.8, 124.3, 122.5, 115.8,
115.0, 113.9, 55.6. Mass (m=z) %: 391 (Mþ, 78%). Anal. calcd. for C22H17NO4S:
C, 67.50; H, 4.38; N, 3.58; S, 8.19%. Found: C, 67.80; H, 4.49; N, 3.35; S, 8.40%.
1-Phenylsulfonyl-(1H-indol-2-yl)(thiophen-2-yl)methanone (3f). Yieꢂld1:
0.45 g (64%). Mp: 136–138 ꢁC. IR (KBr): 1642 (CO), 1359 & 1175 (SO2Ph) cm
.
1H NMR (300 MHz, CDCl3): d 8.13 (d, J ¼ 7.5 Hz, 3H, Ar-H), 7.76 (d, J ¼ 5.7 Hz,
2H, Ar-H), 7.57 (t, J ¼ 7.2 Hz, 2H, Ar-H), 7.48 (t, J ¼ 7.2 Hz, 3H, Ar-H), 7.32–
7.25 (m, 1H, Ar-H), 7.17 (t, J ¼ 7.2 Hz, 1H, Ar-H), 7.07 (s, 1H, Ar-H). 13C NMR
(75 MHz, CDCl3): d 179.0, 144.1, 138.2, 137.8, 137.3, 135.4, 135.2, 134.0, 129.0,
128.4, 128.3, 127.7, 127,1, 124.3, 122.6, 116.6, 115.1. Mass (m=z) %: 367 (Mþ,