J. S. Yadav et al. / Tetrahedron Letters 48 (2007) 7034–7037
7037
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(Table 1). After complete conversion as indicated by TLC,
the reaction mixture was quenched with water (15 mL)
and extracted with dichloromethane (2 · 15 mL). The
combined extracts were dried over anhydrous Na2SO4
and concentrated in vacuo. The resulting crude product
was purified by column chromatography on silica gel
(Merck, 100–200 mesh, ethyl acetate–hexane, 1:9) to
afford 3-(4-chlorophenylthio)-5-methoxyindole (0.078 g,
0.269 mmol, 97%). Spectral data for selected products:
3g: 3-(4-chlorophenylthio)-1H-indole: Pale brownish solid,
mp: 126–130 ꢁC; IR (KBr): mmax 3403, 2923, 1640, 1505,
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11. Typical procedure: A mixture of 5-methoxyindole (0.04 g,
0.28 mmol), 4-chlorothiophenol (0.04 g, 0.28 mmol) and
SelectfluorTM (0.1 g, 0.28 mmol) in acetonitrile (5 mL) was
stirred at room temperature for the appropriate time
1473, 1452, 1090, 1008, 811, 745 cmÀ1
.
1H NMR
(300 MHz, CDCl3): d 8.33 (br s, 1H), 7.32–7.58 (m, 4H),
6.89–7.20 (m, 5H). 13C NMR (75 MHz, CDCl3): d 100.6,
111.5, 119.5, 121.1, 123.4, 127.5, 128.7, 130.6. LC–MS:
m/z (%): 260 (M+1, 45), 161 (100), 177 (30), 169 (20), 149
(15), 117 (10), 101 (5). HRMS calcd for C14H10NSCl:
259.0144. Found: 259.0141. Compound 3h: 3-(4-chloro-
phenylthio)-5-methoxy-1H-indole: Pale brownish solid,
mp: 97–105 ꢁC; IR (KBr): mmax 3406, 2922, 2852, 1632,
1
1581, 1475, 1285, 1206, 1090, 1030, 813 cmÀ1. H NMR
(300 MHz, CDCl3): d 8.36 (br s, 1H), 7.41 (s, 1H), 7.20–
7.33 (m, 2H), 7.02–7.18 (m, 1H), 6.77–7.03 (m, 4H), 3.78
(s, 3H). 13C NMR (75 MHz, CDCl3): d 47.2, 99.3, 101.5,
106.5, 109.5, 125.7, 125.9, 126.0, 126.8, 128.0, 128.1, 128.2,
155.2. LC–MS: m/z (%): 289 (M+, 30), 279 (20), 257 (10),
197 (20), 169 (15), 147 (100), 117 (10). HRMS calcd for
C15H12NOSCl: 289.0249. Found: 289.0250. Compound 3l:
3-(p-tolylthio)-2-methyl–1H-indole: Liquid, IR (KBr):
mmax 3395, 2924, 2854, 1735, 1626, 1456, 1220, 1082,
1019, 803, 764 cmÀ1. 1H NMR (300 MHz, CDCl3): d 8.20
(br s, 1H), 7.44–7.55 (m, 1H), 7.20–7.29 (m, 1H), 6.99–7.17
(m, 2H), 6.83–6.96 (m, 4H), 2.50 (s, 3H), 2.24 (s, 3H). 13
C
NMR (75 MHz, CDCl3): d 12.1, 20.7, 100.0, 110.5, 119.0,
120.6, 122.1, 125.8, 129.4, 130.3, 135.4, 135.6, 140.8. LC–
MS: m/z (%): 254 (M+1, 100), 175 (40), 140 (20). HRMS
calcd for C16H16NS (M+H+): 254.1003. Found: 254.1011.
Compound 3m: 3-(4-chlorophenylthio)-2-methyl-1H-
indole: Liquid, IR (KBr): mmax 3393, 2920, 2851, 1576,
1542, 1473, 1455,1088, 1009, 814, 745 cmÀ1 1H NMR
.
(300 MHz, CDCl3): d 8.20 (br s, 1H), 7.44–7.55 (m, 1H),
7.02–7.32 (m, 5H), 6.86–6.99 (m, 2H), 2.50 (s, 3H). 13C
NMR (75 MHz, CDCl3): d 12.1, 99.1, 110.7, 118.8, 120.8,
122.3, 126.7, 128.7, 130.0, 130.3, 135.4, 137.9, 141.1. LC–
MS: m/z (%): 274 (M+1, 100), 260 (50), 206 (35), 132 (20),
120 (10). HRMS calcd for C15H13NSCl (M+H+):
274.0457. Found: 274.0459.