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1-(4-Methoxyphenyl)-2-(pyridin-3-yl)-1H-pyrrole-3-carbaldehyde
(5n). Red oily liquid (58 mg, 70%); H NMR (400 MHz, CDCl3) pyrrole-3-carbaldehyde (7d). Yellow solid (115 mg, 70%, mp ¼
2-(5-Bromo-1-tosyl-1H-indol-3-yl)-1-(4-methoxyphenyl)-1H-
1
1
ꢀ
d 3.81 (s, 3H), 6.85 (d, J ¼ 8.9 Hz, 2H), 6.91 (d, J ¼ 3.0 Hz, 1H), 139–141 C); H NMR (400 MHz, CDCl3) d 2.38 (s, 3H), 3.79 (s,
6.96 (d, J ¼ 2.9 Hz, 1H), 7.04 (d, J ¼ 8.9 Hz, 2H), 7.28 (t, J ¼ 3H), 6.72 (d, J ¼ 8.9 Hz, 2H), 6.89 (d, J ¼ 3.2 Hz, 1H), 6.97 (d, J ¼
3.7 Hz, 1H), 7.54 (d, J ¼ 7.8 Hz, 1H), 8.5 (bs, 1H), 8.58 (d, J ¼ 2.5 Hz, 1H), 7.00 (d, J ¼ 8.9 Hz, 2H), 7.24 (d, J ¼ 8.0 Hz, 2H), 7.30
4.7 Hz, 1H), 9.72 (s, 1H); 13C NMR (75 MHz, CDCl3) d 55.4, 108.4, (d, J ¼ 1.7 Hz, 2H), 7.37 (d, J ¼ 7.0 Hz, 1H), 7.45 (s, 1H), 7.60 (d, J
114.5 (2C), 122.9, 125.1, 125.7, 125.7, 127.3 (2C), 131.0, 137.8, ¼ 8.4 Hz, 2H), 7.81 (d, J ¼ 8.8 Hz, 1H), 9.57 (s, 1H); 13C NMR (400
137.9, 149.4, 151.0, 159.2, 186.0; IR (KBr)/cmꢂ1, 2954, 1666, MHz, CDCl3) d 29.6, 55.5, 108.5, 110.9, 114.4 (2C), 115.0, 117.5,
1512, 1242, 1033; HRMS (ESI): calcd for C17H14N2O2 (MH+) 123.1, 125.8, 125.9, 126.6 (2C), 126.8 (2C), 128.3, 128.3, 130.1
279.1133; found 279.1140.
(2C), 131.5, 131.8, 132.3, 133.1, 134.4, 145.7, 159.1, 185.8; IR
2-(Furan-2-yl)-1-(4-methoxyphenyl)-1H-pyrrole-3-carbaldehyde (KBr)/cmꢂ1, 2924, 2854, 1720, 1666, 1512, 1250, 1119; HRMS
(5o). Red oily liquid (51 mg, 64%); H NMR (400 MHz, CDCl3) (ESI): calcd for C27H21BrN2O4S (MH+) 549.0483; found 549.0488.
1
d 3.85 (s, 3H), 6.05 (d, J ¼ 3.3 Hz, 1H), 6.37 (d, J ¼ 3.2 Hz, 1H),
2-(5-Chloro-1-tosyl-1H-indol-3-yl)-1-(4-methoxyphenyl)-1H-
6.93 (d, J ¼ 8.8 Hz, 2H), 7.18 (d, J ¼ 8.8 Hz, 3H), 7.99 (d, J ¼ pyrrole-3-carbaldehyde (7e). Brown solid (102 mg, 68%, mp ¼
7.7 Hz, 1H), 8.05 (d, J ¼ 7.9 Hz, 1H), 10.08 (s, 1H); 13C NMR (75 134–136 C); H NMR (400 MHz, CDCl3) d 2.17 (s, 3H), 3.58 (s,
1
ꢀ
MHz, CDCl3) d 55.5, 108.1, 111.2, 111.7, 114.3 (2C), 126.0, 127.2 3H), 6.52 (d, J ¼ 8.9 Hz, 2H), 6.67 (d, J ¼ 3.1 Hz, 1H), 6.76 (dd, J ¼
(2C), 127.9, 131.8, 133.1, 141.7, 143.4, 159.4, 187.4; IR (KBr)/ 2.4 Hz, 1H), 6.80 (d, J ¼ 8.9 Hz, 2H), 6.95 (d, J ¼ 1.9 Hz, 1H),
cmꢂ1, 2970, 1682, 1582, 1466, 1265, 1011; HRMS (ESI): calcd for 7.02–7.05 (m, 4H), 7.40 (d, J ¼ 8.4 Hz, 2H), 7.65 (d, J ¼ 8.8 Hz,
C
16H13NO3 (MH+) 268.0974; found 268.0980.
1H), 9.36 (s, 1H); 13C NMR (75 MHz, CDCl3) d 29.7, 55.5, 108.4,
1-(4-Methoxyphenyl)-2-(1-tosyl-1H-indol-3-yl)-1H-pyrrole-3-
111.0, 114.4 (2C), 114.6, 120.0, 125.6, 125.8, 125.9, 126.6 (2C),
carbaldehyde (7a). Yellow solid (107 mg, 76%, mp ¼ 119–121 126.8 (2C), 128.5, 130.0, 130.1 (2C), 131.4, 131.5, 132.5, 132.8,
ꢀC); 1H NMR (400 MHz, CDCl3) d 2.37 (s, 3H), 3.78 (s, 3H), 6.71 134.5, 145.6, 159.1, 185.8; IR (KBr)/cmꢂ1, 2924, 2854, 1666,
(d, J ¼ 8.9 Hz, 2H), 6.9 (d, J ¼ 3.1 Hz, 1H), 6.97 (d, J ¼ 2.4 Hz, 1H), 1512, 1250, 1173; HRMS (ESI): calcd for C27H21ClN2O4S (MH+)
7.02 (d, J ¼ 8.9 Hz, 2H), 7.12–7.16 (m, 1H), 7.23 (d, J ¼ 8 Hz, 3H), 505.0911; found 505.0916.
7.28–7.32 (m, 1H), 7.44 (s, 1H), 7.63 (d, J ¼ 8.3 Hz, 2H), 7.95 (d, J
1-(4-Methoxyphenyl)-2-(1-(phenylsulfonyl)-1H-indol-3-yl)-1H-
¼ 8.3 Hz, 1H), 9.58 (s, 1H); 13C NMR (75 MHz, CDCl3) d 29.6, pyrrole-3-carbaldehyde (7f). Brown solid (96 mg, 70%, mp ¼
55.4, 108.1, 111.5, 113.5, 114.3 (2C), 120.3, 123.9, 125.2, 125.7, 117–119 ꢀC); 1H NMR (400 MHz, CDCl3), d 3.77 (s, 3H), 6.69 (d, J
125.8, 126.5 (2C), 126.8 (2C), 127.1, 129.9 (2C), 130.2, 131.7, ¼ 8.93 Hz, 2H), 6.89 (d, J ¼ 3.1 Hz, 1H), 6.96 (d, J ¼ 3.3 Hz, 1H),
133.3, 134.4, 134.7, 145.3, 158.9, 186.1; IR (KBr)/cmꢂ1, 2924, 7.00 (d, J ¼ 8.9 Hz, 2H), 7.12–7.16 (m, 1H), 7.23 (d, J ¼ 7.6 Hz,
2854, 1659, 1597, 1512, 1173; HRMS (ESI): calcd for 1H), 7.28–7.32 (m, 1H), 7.42–7.46 (m, 3H), 7.54–7.59 (m, 1H),
C
27H22N2O4S (MH+) 471.1378; found 471.1382.
7.72–7.74 (m, 2H), 7.96 (d, J ¼ 8.3 Hz, 1H), 9.58 (s, 1H); 13C NMR
3-(3-Formyl-1-(4-methoxyphenyl)-1H-pyrrol-2-yl)-1-tosyl-
(75 MHz, CDCl3), d 55.4, 108.1, 111.7, 113.4, 114.3 (2C), 120.3,
1H-indole-5-carbonitrile (7b). Brown solid (101 mg, 73%, mp 123.9, 125.3, 125.7, 126.5 (2C), 126.6 (2C), 127.1, 129.3 (2C),
¼ 123–125 ꢀC); 1H NMR (400 MHz, CDCl3) d 2.40 (s, 3H), 3.79 (s, 130.2, 131.6, 132.2, 134.0, 134.4 (2C), 137.6, 158.8, 186.1; IR
3H), 6.73 (d, J ¼ 8.9 Hz, 2H), 6.90 (d, J ¼ 3.1 Hz, 1H), 7.00–703 (KBr)/cmꢂ1, 2932, 2839, 1720, 1666, 1512, 1225, 1180; HRMS
(m, 3H), 7.28 (d, J ¼ 8.0 Hz, 2H), 7.45 (d, J ¼ 8.8 Hz, 1H), 7.52 (ESI): calcd for C26H20N2O4S (MH+) 457.1222; found 457.1226.
(dd, J ¼ 7.1 Hz, 1H), 7.64 (s, 1H), 7.67 (d, J ¼ 8.4 Hz, 2H), 8.05 (d,
2-(5-Methoxy-1-(phenylsulfonyl)-1H-indol-3-yl)-1-(4-methox-
J ¼ 8.1 Hz, 1H), 9.60 (s, 1H); 13C-NMR (75 MHz, CDCl3) d 29.6, yphenyl)-1H-pyrrole-3-carbaldehyde (7g). Yellow viscous liquid
55.5, 109.1, 111.4, 114.4, 114.5 (2C), 125.4, 126.0, 126.5 (2C), (99 mg, 68%); 1H NMR (400 MHz, CDCl3) d 3.64 (s, 3H), 3.77 (s,
126.9 (2C), 128.1, 128.1, 129.1, 129.2, 129.8, 130.2, 130.3 (2C), 3H), 6.56 (d, J ¼ 2.4 Hz, 1H), 6.70 (d, J ¼ 8.9 Hz, 2H), 6.88–6.91
130.9, 131.3, 134.1, 136.0, 146.2, 159.1, 185.5; IR (KBr)/cmꢂ1
,
(m, 2H), 6.98 (d, J ¼ 2.4 Hz, 1H), 7.00 (d, J ¼ 8.9 Hz, 2H), 7.42–
2924, 2854, 2230, 1720, 1666, 1512, 1173; HRMS (ESI): calcd for 7.45 (m, 3H), 7.54–7.59 (m, 1H), 7.71–7.73 (m, 2H), 7.84 (d, J ¼
C
28H21N3O4S (MH+) 496.1331; found 496.1336.
9.1 Hz, 1H), 9.58 (s, 1H); 13C NMR (75 MHz, CDCl3) d 55.4, 55.5,
2-(5-Methoxy-1-tosyl-1H-indol-3-yl)-1-(4-methoxyphenyl)-1H-
102.0, 108.2, 111.8, 114.3 (2C), 114.5, 115.0, 125.6, 125.8, 126.3
pyrrole-3-carbaldehyde (7c). Red solid (105 mg, 70%, mp ¼ 127– (2C), 126.6 (2C), 127.8, 129.1, 129.3 (2C), 131.1, 131.7, 133.3,
1
129 C); H NMR (400 MHz, CDCl3) d 2.37 (s, 3H), 3.64 (s, 3H), 134.0, 137.6, 156.9, 158.9, 186.1; IR (KBr)/cmꢂ1, 2924, 2854,
ꢀ
3.78 (s, 3H), 6.57 (d, J ¼ 2.4 Hz, 1H), 6.71 (d, J ¼ 8.9 Hz, 2H), 1728, 1666, 1512, 1466, 1250, 1180; HRMS (ESI): calcd for
6.88–6.9 (m, 2H), 6.98 (d, J ¼ 2.7 Hz, 1H), 7.02 (d, J ¼ 8.9 Hz, 2H),
7.22 (d, J ¼ 8.2 Hz, 2H), 7.43 (s, 1H), 7.62 (d, J ¼ 8.4 Hz, 2H), 7.82
C
27H22N2O5S (MH+) 487.1327; found 487.1332.
2-(5-Bromo-1-(phenylsulfonyl)-1H-indol-3-yl)-1-(4-methoxyphenyl)-
(d, J ¼ 9.1 Hz, 1H), 9.58 (s, 1H); 13C-NMR (75 MHz, CDCl3) 1H-pyrrole-3-carbaldehyde (7h). Brownish yellow gummy liquid
d 21.5, 55.4, 55.5, 102.0, 108.2, 111.5, 114.3 (2C), 114.5, 115.0, (107 mg, 67%); 1H NMR (400 MHz, CDCl3) d 3.82 (s, 3H), 3.76 (d,
125.6, 125.8, 126.3 (2C), 126.7 (2C), 127.9, 129.1, 129.9 (2C), J ¼ 8.9 Hz, 2H), 6.91 (d, J ¼ 3.1 Hz, 1H), 7.00 (d, J ¼ 3.1 Hz, 1H),
131.1, 131.8, 132.4, 134.7, 145.2, 156.8, 158.9, 186.1; IR (KBr)/ 7.3 (d, J ¼ 8.9 Hz, 2H), 7.35 (d, J ¼ 1.5 Hz, 1H), 7.42 (d, J ¼ 6.9 Hz,
cmꢂ1, 2924, 2854, 1720, 1659, 1512, 1173; HRMS (ESI): calcd 1H), 7.48–7.51 (m, 3H), 7.60–7.65 (m, 1H), 7.74 (d, J ¼ 7.3 Hz,
forC28H24N2O5S (MH+) 501.1484; found 501.1488.
2H), 7.86 (d, J ¼ 8.8 Hz, 1H), 9.60 (s, 1H); 13C NMR (75 MHz,
CDCl3) d 55.5, 108.4, 111.1, 114.4 (2C), 114.9, 117.6, 123.1, 123.9,
15454 | RSC Adv., 2018, 8, 15448–15458
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