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HETEROCYCLES, Vol. 82, No. 2, 2011
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(s, 1H), 5.18 (s, 2H), 3.64 (s, 3H); C NMR (CDCl3) δ 139.7, 137.0, 135.6, 134.0, 133.8, 132.1, 131.5,
129.3, 128.6, 128.4, 128.4, 127.7, 127.5, 127.2, 126.9, 126.7, 126.3, 121.5, 120.8, 119.1, 110.7, 110.5,
109.2, 74.0, 48.8, 32.9; HRMS (ESI+) m/z calculated for C32H27N2 (MH+) 439.2174, found 439.2172.
3-(1-Benzyl-2,5-diphenyl-1H-pyrrol-3-yl)-1-(phenylsulfonyl)-1H-indole (26): Light orange solid, 81%
1
yield; H NMR (CDCl3) δ 8.05 (d, 1H, J = 8.3 Hz), 7.78 (d, 1H, J = 7.8 Hz), 7.67 (d, 2H, J = 7.8 Hz),
7.52-7.17 (m, 18H), 7.13 (s, 1H), 6.77-6.74 (m, 3H), 5.22 (s, 2H), 13C NMR (CDCl3) δ 139.3, 138.3,
136.0, 135.4, 133.7, 133.5, 132.9, 131.4, 131.2, 129.4, 129.3, 128.8, 128.7, 128.6, 127.9, 127.4, 127.2,
124.8, 123.5, 123.0, 121.3, 118.9, 114.5, 113.9, 110.1, 48.9; HRMS (ESI+) m/z calculated for
C37H29N2O2S (MH+) 565.1950, found 565.1942.
1
3-(1-Benzyl-2,5-dimethyl-1H-pyrrol-3-yl)- 1H-indole (27): Light yellow solid, 84% yield; H NMR
(CDCl3) δ 8.07 (br s, 1H), 7.80 (d, 1H, J = 7.8 Hz), 7.41-7.14 (m, 7H), 7.00 (d, 2H, J = 7.6 Hz), 6.23 (s,
1H), 5.13 (s, 2H), 2.26 (s, 6H); 13C NMR (CDCl3) δ 138.9, 136.4, 129.0, 127.7, 127.3, 126.0, 122.1,
121.6, 120.7, 119.6, 113.5, 113.3, 111.2, 107.6, 47.3, 12.6, 11.4; HRMS (ESI+) m/z calculated for
C21H21N2 (MH+) 301.1705, found 301.1703.
1
3-(1-Benzyl-2,5-dimethyl-1H-pyrrol-3-yl)-1-methyl-1H-indole (28): Yellow solid, 75% yield; H
NMR (CDCl3) δ 7.82 (d, 1H, J = 7.8 Hz), 7.39-7.26 (m, 5H), 7.18 (t, 1H, J = 6.8 Hz), 7.15-7.01 (m, 3H)
6.24 (s, 1H), 5.15 (s, 2H)3.84 (s, 3H), 2.28 (s, 6H); 13C NMR (CDCl3) δ 138.9, 137.1, 129.0, 128.1, 127.6,
127.3, 126.4, 126.0, 124.5, 121.7, 120.9, 119.1, 113.4, 112.0, 109.3, 107.6, 47.3, 33.0, 12.6, 11.5; HRMS
(ESI+) m/z calculated for C22H23N2 (MH+) 315.1861, found 315.1856.
3-(1-Benzyl-2,5-dimethyl-1H-pyrrol-3-yl)-1-(phenylsulfonyl)-1H-indole (29): Orange solid, 68%
yield; 1H NMR (CDCl3) δ 8.09 (d, 2H, J = 8.3 Hz), 7.96-7.90 (m, 3H), 7.74 (d, 2H, J = 7.8 Hz), 7.54-7.25
13
(m, 6H), 6.98 (d, 2H, J = 8.0 Hz), 6.19 (s, 1H), 5.12 (s, 2H), 2.23 (s, 6H); C NMR (CDCl3) δ 138.4,
138.3, 135.6, 133.9, 131.6, 129.4, 129.1, 128.4, 127.7, 127.0, 125.9, 125.4, 123.5, 122.2, 121.4, 120.0,
113.9, 111.0, 107.1, 47.3, 12.6, 11.4; HRMS (ESI+) m/z calculated for C27H25N2O2S (MH+) 441.1637,
found 441.1631.
2-(1-Benzyl-2,5-diphenyl-1H-pyrrol-3-yl)-1H-indole (30): White solid, 92% yield; 1H NMR (CDCl3) δ
7.73 (br s, 1H), 7.56-7.36 (m, 11H), 7.20-7.07 (m, 6H), 6.77-6.75 (m, 3H), 6.47 (s, 1H), 5.12 (s, 2H); 13C
NMR (CDCl3) δ 139.1, 136.3, 136.0, 134.7, 133.3, 132.9, 131.9, 131.6, 129.4, 129.3, 129.1, 129.0, 128.8,
128.6, 127.8, 127.2, 126.2, 121.2, 120.0, 119.9, 115.6, 110.5, 108.3, 98.7, 48.7; HRMS (ESI+) m/z