J. Liu et al. / Tetrahedron 67 (2011) 3420e3426
3425
1014, 944, 805, 735, 563, 497 cmꢁ1. HRMS (ESI) ([M]þ) calcd for
C25H26N2: 354.2096, found: 354.2097.
132.1, 129.8, 129.4, 129.0, 128.5, 127.3, 121.4, 120.0, 118.6, 114.8, 112.5,
110.8, 108.9, 55.0, 47.7, 40.7, 32.6. IR (KBr): 3044, 2928, 1728, 1605,
1475,1365,1332,1257,1129,1049,1006, 870, 779, 738, 695, 567 cmꢁ1
.
4.3.4. 4-((1H-Indol-3-yl)(p-tolyl)methyl)-N,N-dimethylaniline
HRMS (ESI) ([M]þ) calcd for C25H26N2O: 370.2045, found: 370.2047.
(4d). White solid, mp 164e165 ꢀC. 1H NMR (400 MHz, CDCl3):
d
7.85 (s, 1H), 7.30e7.22 (m, 2H), 7.13e7.05 (m, 6H), 6.97 (d,
J¼7.8 Hz, 2H), 6.66 (d, J¼8.0 Hz, 2H), 6.53 (s,1H), 5.54 (s,1H), 2.89 (s,
6H), 2.30 (s, 3H). 13C NMR (100 MHz, CDCl3):
148.9, 141.6, 136.6,
4.3.10. 4-((1H-Indol-3-yl)(3-methoxyphenyl)methyl)-N,N-dimethy-
laniline (4j). White solid, mp 151e153 ꢀC. 1H NMR (400 MHz,
d
CDCl3):
d
7.93 (s, 1H), 7.32 (d, J¼8.0 Hz, 1H), 7.25 (d, J¼8.2 Hz, 1H),
135.3, 132.4, 129.4, 128.8, 128.7, 127.0, 123.9, 121.8, 120.7, 120.0,
119.2, 112.6, 110.9, 47.3, 40.8, 29.7. IR (KBr): 3735, 3587, 3397, 3186,
3047, 2890, 2858, 2814, 2360, 2341, 1615, 1518, 1457, 1418, 1355,
1338,1162,1093,1022, 943, 802, 761, 668, 631, 574, 532 cmꢁ1. HRMS
(ESI) ([M]þ) calcd for C24H24N2: 340.1939, found: 340.1937.
7.18e7.14 (m, 2H), 7.10e7.08 (m, 2H), 6.97 (t, J¼8.4 Hz, 1H),
6.83e6.80 (m, 2H), 6.74 (d, J¼7.8 Hz, 1H), 6.67 (d, J¼8.0 Hz, 2H),
6.60e6.59 (m, 1H), 5.55 (s, 1H), 3.72 (s, 3H), 2.91 (s, 6H). 13C NMR
(100 MHz, CDCl3):
d 159.4, 146.4, 136.6, 129.5, 129.0, 127.0, 123.9,
121.9, 121.5, 120.3, 120.0, 119.2, 114.9, 112.6, 111.0, 110.9, 55.0, 47.8,
40.8. IR (KBr): 3223, 3042, 2921, 2858, 1609, 1516, 1449, 1328, 1271,
4.3.5. 4-((4-Methoxyphenyl)(1-methyl-1H-indol-3-yl)methyl)-
1216, 1133, 1092, 1048, 934, 809, 765, 733, 692, 594, 531 cmꢁ1
.
N,N-dimethylaniline (4e). White solid, mp 155e156 ꢀC. 1H NMR
HRMS (ESI) ([M]þ) calcd for C24H24N2O: 356.1889, found: 356.1888.
(400 MHz, CDCl3):
d
7.26e7.12 (m, 5H), 7.08 (d, J¼8.2 Hz, 2H), 6.95
(t, J¼7.8 Hz, 1H), 6.79 (d, J¼8.4 Hz, 2H), 6.67 (d, J¼8.0 Hz, 2H), 6.40
4.3.11. 4-((2-Chlorophenyl)(1H-indol-3-yl)methyl)-N,N-dimethylani-
(s, 1H), 5.52 (s, 1H), 3.75 (s, 3H), 3.65 (s, 3H), 2.90 (s, 6H). 13C NMR
line (4k). White solid, mp 152e153 ꢀC. 1H NMR (400 MHz, CDCl3):
(100 MHz, CDCl3):
d
157.7, 148.8, 137.4, 137.0, 129.7, 129.4, 128.5,
d
7.92 (s, 1H), 7.37 (d, J¼8.0 Hz, 1H), 7.33 (d, J¼8.0 Hz, 1H), 7.22 (d,
127.4, 121.4, 120.1, 119.2, 118.6, 113.4, 112.6, 108.9, 55.1, 46.9, 40.8,
32.6. IR (KBr): 3042, 2924, 2813, 1694, 1608, 1467, 1338, 1246, 1167,
1119, 1029, 944, 807, 740, 568, 522 cmꢁ1. HRMS (ESI) ([M]þ) calcd
for C25H26N2O: 370.2050, found: 370.2050.
J¼8.2 Hz, 1H), 7.17e7.12 (m, 2H), 7.11e7.05 (m, 4H), 6.98 (t, J¼7.8 Hz,
1H), 6.72 (d, J¼8.4 Hz, 2H), 6.54 (s, 1H), 6.00 (s, 1H), 2.92 (s, 6H). 13C
NMR (100 MHz, CDCl3):
d 149.0, 141.9, 136.7, 134.0, 130.5, 130.3,
129.7,129.4,127.3,126.9, 126.5, 122.0,119.8,119.6,119.3,112.4,110.9,
44.1, 40.6. IR (KBr): 3254, 2936, 2856, 1606, 1561, 1514, 1460, 1324,
1208, 1129, 1042, 937, 806, 751, 603, 560 cmꢁ1. HRMS (ESI) ([M]þ)
calcd for C23H21ClN2: 360.1388, found: 360.1390.
4.3.6. 4-((1H-Indol-3-yl)(4-methoxyphenyl)methyl)-N,N-dimethyla-
niline (4f). White solid, mp 162e164 ꢀC. 1H NMR (400 MHz, CDCl3):
d
7.92 (s, 1H), 7.33 (d, J¼8.4 Hz, 1H), 7.26e7.24 (m, 1H), 7.17e7.13 (m,
3H), 7.08 (d, J¼8.0 Hz, 2H), 6.97 (t, J¼8.2 Hz, 1H), 6.80 (d, J¼7.8 Hz,
2H), 6.67 (d, J¼8.0 Hz, 2H), 6.56 (s,1H), 5.53 (s,1H), 3.77 (s, 3H), 2.91
4.3.12. 4-(1-(1H-Indol-3-yl)butyl)-N,N-dimethylaniline (4l). Light yel-
low oil. 1H NMR (400 MHz, CDCl3):
d
7.86 (s, 1H), 7.47 (d, J¼8.4 Hz,
(s, 6H). 13C NMR (100 MHz, CDCl3):
d
157.7, 148.9, 136.9, 136.6, 132.5,
1H), 7.27 (d, J¼8.0 Hz, 1H), 7.17e7.09 (m, 3H), 7.02e6.95 (m, 2H), 6.67
(d, J¼8.2 Hz, 2H), 4.08 (t, J¼8.0 Hz, 1H), 2.88 (s, 6H), 2.12e2.09
(m, 1H), 1.97e1.95 (m, 1H), 1.35e1.33 (m, 2H), 0.92 (t, J¼6.4 Hz, 3H).
129.8, 129.4, 127.0, 123.9, 121.8, 120.8, 120.0, 119.1, 113.4, 112.6,110.9,
55.2, 46.9, 40.7. IR (KBr): 3411, 3171, 3059, 3029, 2958, 2890, 2854,
2833, 2360, 1610, 1508, 1473, 1338, 1314, 1244, 1218, 1201, 1134,
1031,1007, 942, 839, 773, 577, 518 cmꢁ1. HRMS (ESI) ([M]þ) calcd for
C24H24N2O: 356.1889, found: 356.1886.
13C NMR (100 MHz, CDCl3):
d 148.8, 136.4, 133.8, 128.4, 127.1, 121.7,
121.3, 120.7, 119.6, 118.9, 112.7, 110.9, 41.4, 40.8, 38.5, 21.2, 14.2. IR
(KBr): 3130, 2752, 2460, 1861, 1616, 1501, 1432, 1302, 1246, 1048, 930,
781, 711, 647, 542 cmꢁ1. HRMS (ESI) ([M]þ) calcd for C20H24N2:
292.1939, found: 292.1936.
4.3.7. 4-((4-Chlorophenyl)(1-methyl-1H-indol-3-yl)methyl)-N,N-di-
methylaniline (4g). White solid, mp 157e158 ꢀC. 1H NMR (400 MHz,
CDCl3):
d
7.26 (d, J¼8.0 Hz, 1H), 7.22e7.19 (m, 4H), 7.15 (d, J¼8.8 Hz,
4.3.13. 4-((1H-Indol-3-yl)methyl)-N,N-dimethylaniline (4m)3. Light
2H), 7.05 (d, J¼8.2 Hz, 2H), 6.96 (t, J¼7.8 Hz, 1H), 6.66 (d, J¼8.0 Hz,
yellow oil. 1H NMR (400 MHz, CDCl3):
d 7.86 (s, 1H), 7.54 (d,
2H), 6.39 (s, 1H), 5.53 (s, 1H), 3.66 (s, 3H), 2.90 (s, 6H). 13C NMR
J¼8.2 Hz, 1H), 7.30 (d, J¼8.0 Hz, 1H), 7.21e7.14 (m, 3H), 7.06 (t,
(100 MHz, CDCl3):
d 149.0, 143.4, 137.4, 131.6, 131.5, 130.2, 129.4,
J¼8.4 Hz, 1H), 6.83 (s, 1H), 6.70e6.68 (m, 2H), 4.02 (s, 2H), 2.89 (s,
128.6, 128.2, 127.2, 121.6, 119.9, 118.7, 118.4, 112.5, 109.1, 47.1, 40.6,
32.6. IR (KBr): 3048, 2920, 2804, 1610, 1518, 1477, 1340, 1230, 1160,
1124,1086, 1010, 940, 851, 800, 736, 708, 563, 530 cmꢁ1. HRMS (ESI)
([M]þ) calcd for C24H23ClN2: 374.1550, found: 374.1549.
6H). 13C NMR (100 MHz, CDCl3):
d 149.0, 136.4, 129.4, 129.2, 127.4,
122.1, 121.8, 119.2, 116.6, 113.0, 110.9, 40.9, 30.4. IR (KBr): 3240,
2864, 2641, 1826, 1716, 1623, 1512, 1452, 1232, 1234, 1046, 932, 803,
783, 734, 712, 657, 603, 534 cmꢁ1
.
4.3.8. 4-((4-Chlorophenyl)(1H-indol-3-yl)methyl)-N,N-dimethylani-
4.3.14. 4-((1H-Indol-3-yl)(naphthalen-2-yl)methyl)-N,N-dimethyla-
line (4h). White solid, mp 130e132 ꢀC. 1H NMR (400 MHz, CDCl3):
niline (4n). White solid, mp 151e152 ꢀC. 1H NMR (400 MHz, CDCl3):
d
7.87 (s, 1H), 7.29 (d, J¼8.0 Hz,1H), 7.23e7.20 (m, 3H), 7.16e7.13 (m,
d 7.94 (s, 1H), 7.80e7.69 (m, 3H), 7.61 (s, 1H), 7.43e7.40 (m, 3H), 7.35
3H), 7.05 (d, J¼8.4 Hz, 2H), 6.98 (t, J¼8.2 Hz, 1H), 6.66 (d, J¼7.8 Hz,
(d, J¼8.0 Hz, 1H), 7.28 (d, J¼8.4 Hz, 1H), 7.14e7.11 (m, 3H), 6.96 (t,
2H), 6.50 (s, 1H), 5.53 (s, 1H), 2.90 (s, 6H). 13C NMR (100 MHz,
J¼8.2 Hz,1H), 6.68 (d, J¼8.0 Hz, 2H), 6.59 (s,1H), 5.75 (s,1H), 2.91 (s,
CDCl3):
d
149.1, 143.2, 136.6, 131.6, 131.5, 130.2, 129.4, 128.2, 126.8,
6H). 13C NMR (100 MHz, CDCl3):
d 149.1, 142.3, 136.6, 132.1, 131.9,
123.9, 122.0, 120.0, 119.9, 119.3, 112.5, 111.0, 47.1, 40.6. IR (KBr):
3646, 3626, 3606, 3592, 3585, 3565, 3411, 2919, 2848, 2358, 1614,
1518, 1487, 1455, 1384, 1338, 1212, 1161, 1091, 1016, 940, 858, 799,
765, 690, 621, 581, 554 cmꢁ1. HRMS (ESI) ([M]þ) calcd for
C23H21ClN2: 360.1388, found: 360.1388.
129.6, 128.0, 127.9, 127.6, 127.5, 127.0, 126.9, 125.6, 125.2, 121.9,
120.4, 120.0, 119.3, 112.5, 110.9, 40.7, 29.7. IR (KBr): 3410, 3048,
2920, 2848, 1605, 1515, 1452, 1417, 1343, 1216, 1132, 1091, 1009, 950,
803, 744, 580 cmꢁ1. HRMS (ESI) ([M]þ) calcd for C27H24N2:
376.1939, found: 376.1942.
4.3.9. 4-((3-Methoxyphenyl)(1-methyl-1H-indol-3-yl)methyl)-N,N-di-
4.3.15. 3-Methoxy-N,N-dimethyl-4-((1-methyl-1H-indol-3-yl)(phenyl)
methylaniline (4i). White solid, mp 171e173 ꢀC. 1H NMR (400 MHz,
methyl)aniline (4o). White solid, mp 153e155 ꢀC. 1H NMR (400 MHz,
CDCl3):
d
7.25 (d, J¼7.8 Hz, 2H), 7.19e7.15 (m, 2H), 7.09 (d, J¼8.0 Hz,
CDCl3): d 7.26e7.22 (m, 6H), 7.16e7.14 (m, 2H), 6.96e6.94 (m, 1H),
2H), 6.97e6.93 (m, 1H), 6.84e6.80 (m, 2H), 6.75e6.71 (m, 1H), 6.66
(d, J¼8.2 Hz, 2H), 6.43 (s, 1H), 5.54 (s, 1H), 3.70 (s, 3H), 3.64 (s, 3H),
6.86e6.83 (m, 1H), 6.38 (s, 1H), 6.29 (s, 1H), 6.19 (d, J¼8.4 Hz, 1H),
5.96 (s, 1H), 3.73 (s, 3H), 3.61 (s, 3H), 2.91 (s, 6H). 13C NMR (100 MHz,
2.89 (s, 6H). 13C NMR (100 MHz, CDCl3):
d
159.4, 148.9, 146.5, 137.3,
CDCl3): d 157.5, 150.2, 144.9, 137.3, 130.2, 128.8, 128.6, 127.8, 127.5,