A revisit to the multi-component reaction of indole, aldehyde, and N-substituted aniline…
112.3, 109.1, 47.3, 32.6, 30.8 ppm; HRMS (ESI): exact
mass calculated for C23H21ClN2 ([M ? H]?) 361.1472,
found 361.1462.
mꢀ = 3415, 2924, 2855, 1615, 1517, 1457, 1408, 1319, 1265,
1
1123, 919, 804, 742, 700, 606 cm-1; H NMR (300 MHz,
CDCl3): d = 7.86 (bs, 1H), 7.28–7.10 (m, 8H), 7.03–6.93
(m, 3H), 6.55–6.50 (m, 3H), 5.99–5.86 (m, 1H), 5.54 (s,
1H), 5.28–5.22 (m, 1H), 5.15–5.13 (m, 1H), 4.42 (bs, 1H),
3.71 (d, J = 5.7 Hz, 2H) ppm; 13C NMR (75 MHz,
CDCl3): d = 146.2, 144.6, 136.6, 135.5, 133.2, 129.7,
128.9, 128.1, 127.0, 125.9, 124.0, 121.9, 120.4, 120.0,
119.2, 116.2, 113.0, 111.0, 47.9, 46.8 ppm; HRMS (ESI):
exact mass calculated for C24H22N2 ([M ? H]?) 339.1861,
found 339.1863.
4-[(3-Chlorophenyl)(1-methyl-1H-indol-3-yl)methyl]-N-
methylaniline (4l, C23H21ClN2) Brown solid; yield: 89%
(320 mg); m.p.: 92–94 °C; Rf = 0.33 (hexane/EtOAc,
ꢀ
5:1); IR (KBr): m = 3435, 2928, 2858, 2831, 1629, 1245,
1068, 1020, 739 cm-1 1H NMR (500 MHz, CDCl3):
;
d = 7.28 (d, J = 8.2 Hz, 1H), 7.25–7.15 (m, 5H), 7.12 (d,
J = 6.3 Hz, 1H), 7.02 (d, J = 7.9 Hz, 2H), 6.98 (t,
J = 7.9 Hz, 1H), 6.55 (d, J = 7.6 Hz, 2H), 6.42 (s, 1H),
5.52 (s, 1H), 3.69 (s, 4H, NCH3 and NH), 2.81 (s, 3H) ppm;
13C NMR (125 MHz, CDCl3): d = 147.7, 147.0, 137.4,
134.0, 132.1, 129.6, 129.4, 128.9, 128.6, 127.2, 127.1,
126.2, 121.6, 119.9, 118.8, 118.2, 112.4, 109.1, 47.6, 32.7,
30.8 ppm; HRMS (ESI): exact mass calculated for C23-
H21ClN2 ([M ? H]?) 361.1472, found 361.1478.
4-[(1H-Indol-3-yl)(phenyl)methyl]-N,N-dimethylaniline (4q)
Yield: 88% (287 mg); m.p.: 152–154 °C (162 °C [30]).
4-[(1H-Indol-3-yl)(phenyl)methyl]-3-methyl-1-phenyl-1H-
pyrazol-5-amine (9) Yield: 22% (83 mg); m.p.:
210–212 °C (211–214 °C [9]).
Acknowledgements MLD is thankful to Science and Engineering
Research Board (SERB), India (Grant no. SB/FT/CS-073/2014) for
the financial support under ‘‘Fast Track’’ Scheme. PKB is also
thankful to SERB, India (Grant no. SB/FT/CS-100/2012) for the
financial support. We acknowledge Dr. S. Karmakar for collecting
single-crystal X-ray data and the Sophisticated Analytical Instru-
mentation Facility (SAIF), GU, for the use of single-crystal X-ray
diffractometer.
4-[(1-Benzyl-1H-indol-3-yl)(phenyl)methyl]-N-methylaniline
(4m) Yield: 84% (337 mg) [38].
4-[(1H-Indol-3-yl)(phenyl)methyl]-N-propylaniline
(4n, C24H24N2) Brown gummy product; yield: 87%
(296 mg); Rf = 0.45 (hexane/EtOAc, 5:1); IR (KBr):
ꢀ
m = 3414, 3057, 2925, 2853, 1615, 1517, 1456, 1384, 1320,
1248, 1175, 1094, 1011, 807, 742, 699, 606 cm-1 1H
;
NMR (300 MHz, CDCl3): d = 7.93 (bs, 1H), 7.33–7.12 (m,
8H), 7.03–6.95 (m, 3H), 6.55–6.52 (m, 3H), 5.55 (s, 1H),
3.18 (bs, 1H), 3.04 (t, J = 7.2 Hz, 2H), 1.68–1.56 (m, 2H),
0.93 (t, J = 7.2 Hz, 3H) ppm; 13C NMR (75 MHz, CDCl3):
d = 146.7, 144.7, 136.6, 132.8, 129.8, 128.4, 128.1, 127.0,
125.9, 123.9, 121.9, 120.5, 120.0, 119.2, 112.7, 110.9,
47.9, 46.0, 22.7, 11.7 ppm; HRMS (ESI): exact mass cal-
culated for C24H24N2 ([M ? H]?) 341.2018, found
341.2017.
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4-[(1H-Indol-3-yl)(phenyl)methyl]-N-benzylaniline
(4o, C28H24N2) Brown solid; yield: 91% (354 mg);
Rf = 0.4 (hexane/EtOAc, 5:1); m.p.: 140–142 °C; IR
ꢀ
(KBr): m = 3438, 3389, 3016, 2926, 2853, 2346, 1617,
1519, 1450, 1321, 1274, 1218, 1180, 1090, 1030, 930, 844,
1
802, 748, 693, 605 cm-1; H NMR (300 MHz, CDCl3):
d = 7.96 (bs, 1H), 7.37–7.14 (m, 13H), 7.05–6.96 (m, 3H),
6.95–6.57 (m, 3H), 5.57 (s, 1H), 4.29 (s, 2H), 3.38 (bs, 1H)
ppm; 13C NMR (75 MHz, CDCl3): d = 146.4, 144.6,
139.4, 136.6, 133.2, 129.7, 128.9, 128.6, 128.1, 127.6,
127.2, 127.0, 125.9, 123.9, 121.9, 120.4, 120.0, 119.2,
112.8, 110.9, 48.6, 47.9 ppm; HRMS (ESI): exact mass
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4-[(1H-Indol-3-yl)(phenyl)methyl]-N-allylaniline
(4p, C24H22N2) White gummy product; yield: 88%
(298 mg); Rf = 0.4 (hexane/EtOAc, 5:1); IR (KBr):
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123