2054
S.-J. Ji et al. / Tetrahedron 60 (2004) 2051–2055
Figure 2. X-ray crystal structure of 3k.
0
.2.2. 3,3 -Bis(indolyl)-4-methylphenylmethane, 3b. Pink
(NH) cm21; H NMR (400 MHz, CDCl ): d 6.34 (s, 1H,
1
4
3
1
0
solid; mp 94–96 8C (lit, 95–97 8C); IR (KBr): n 775,
050, 1215, 1510, 1600, 2930, 3040, 3410 (NH) cm21; 1H
NMR (400 MHz, CDCl ): d 2.32 (s, 3H, Ar–CH ), 5.86 (s,
Ar–CH), 6.66 (s, 2H), 7.02 (t, 2H, J¼8.0 Hz), 7.11–7.23
1
(m, 6H), 7.36–7.43 (m, 4H), 7.96 (br, s, 2H, NH); HRMS
[Found: m/z 356.1071(M ), calcd for C H ClN M,
356.1080].
þ
3
3
23 17
2:
1
2
7
H, Ar–CH), 6.68 (s, 2H), 7.02 (t, 2H, J¼7.2 Hz), 7.1 (d,
H, J¼7.2 Hz), 7.23–7.27 (m, 6H), 7.4 (d, 2H, J¼7.2 Hz),
.93 (br, s, 2H, NH); Anal. calcd for C H ON : C, 85.68;
4.2.7. 2-[Bis-(1H-indol-3-yl)-methyl]-4-chloro-phenol,
3g. Yellow needles; mp 78–80 8C; IR (KBr): n 1039,
095, 1338, 1416, 3410 (NH) cm2 ; H NMR (400 MHz,
CDCl ): d 5.40 (br, s, 1H, OH), 5.96 (s, 1H, Ar–CH), 6.90
2
4
20
2
H, 5.99; N, 8.33. Found: C, 85.37; H, 5.95; N, 8.04.
1
1
1
0
0
indole, 3c. Brown needles; mp 187–189 8C (lit,
4
.2.3. 1H,1 H-3,3 -(4-Methoxy-phenylmethanediyl)-bis-
1
3
0a
(s, 3H), 7.05 (t, 2H, J¼7.2 Hz), 7.12–7.14 (m, 2H), 7.23 (t,
1
3
3
89 8C); IR (KBr): n 1220, 1244, 1455, 1508, 1609, 2928,
2H, J¼7.2 Hz), 7.39 (d, 4H, J¼8.8 Hz), 8.05 (br, s, 2H,
410 (NH) cm2 ; H NMR (400 MHz, CDCl ): d 3.78 (s,
1
1
NH); HRMS [Found: m/z 372.1023(M ), calcd for
C H ClN O M, 372.1029].
þ
3
H, CH ), 5.84 (s, 1H, Ar–CH), 6.66 (s, 2H), 6.82 (d, 2H,
3
23 17
2 :
J¼8.3 Hz), 7.00 (t, 2H, J¼7.3 Hz), 7.17 (t, 2H, J¼7.3 Hz),
.19 (s, 2H), 7.35–7.40 (m, 4H), 7.94 (br, s, 2H, NH); Anal.
calcd for C H N O: C, 81.79; H, 5.72; N, 7.95. Found: C,
7
4.2.8. Benzo[1,3]dioxol-5-yl-di-indol-3-yl-methane, 3h.
1
0a
Yellow solid; mp 89–91 8C (lit,
(KBr): n 1260, 1450, 1715, 3410 (NH) cm2 ; H NMR
400 MHz, CDCl ): d 5.82 (s, 1H, Ar–CH), 5.92 (s, 2H,
89**–91 8C); IR
2
4 20 2
1
1
8
1.72; H, 5.82; N, 7.98.
(
3
0
0
4
.2.4. 1H,1 H-3,3 -(4-Nitro-phenylmethanediyl)-bis-
CH ), 6.70 (s, 2H), 6.74 (d, 1H, J¼8.2 Hz), 6.84 (d, 2H,
2
10a
indole, 3d. Yellow needles; mp 217–219 8C (lit, 220–
22 8C); IR (KBr): n 1340, 1456, 1507, 1592, 3052, 3422
J¼8.2 Hz), 7.02 (t, 2H, J¼7.3 Hz), 7.18 (t, 2H, J¼7.3 Hz),
2
(
7.36–7.42 (m, 4H), 7.95 (br, s, 2H, NH); HRMS [Found:
NH) cm2 ; H NMR (400 MHz, CDCl ): d 6.00 (s, 1H,
Ar–CH), 6.70 (s, 2H), 7.00–7.05 (m, 3H), 7.35 (d, 3H,
1
1
þ
m/z 366.1355(M ), calcd for C H N O M, 366.1368].
24 18 2 2:
3
0
Brown solid; mp 322–325 8C (lit, 325 8C); IR (KBr): n
J¼8.0 Hz), 7.40 (d, 2H, J¼8.0 Hz), 7.52 (d, 2H, J¼8.8 Hz),
4.2.9.
3,3 -Bis(indolyl)-4-methylphenylmethane,
0a
3i.
1
8
C H N O : C, 75.19; H, 4.66; N, 11.44. Found: C, 75.28;
.04 (br, s, 2H, NH), 8.15 (d, 2H, J¼8.8 Hz); Anal. calcd for
1260, 1450, 1715, 3410 (NH) cm2 ; H NMR (400 MHz,
1 1
2
3 17 3 2
H, 4.51; N, 11.60.
CDCl ): d 5.95 (s, 1H, Ar–CH), 6.90 (s, 2H), 7.03–7.50 (m,
3
11H), 8.00 (br, s, 2H, NH); HRMS [Found: m/z
312.1255(M ), calcd for C H N O M, 312.1263].
þ
4.2.5. (4-Chloro-phenyl)-(1H-indol-3-yl)-methyl]-
phenyl-amine, 3e. Pink solid; mp 76–77 8C; IR (KBr): n
2
1 16 2 :
2
1
1
1
(
089, 1455, 1487, 3054, 3410 (NH) cm
;
H NMR
400 MHz, CDCl ): d 5.86 (s, 1H, Ar–CH), 6.66 (s, 2H),
4.2.10. Diindol-3-yl-[2]thienyl-methane, 3j. Brown solid;
1
0a
mp 151–153 8C (lit,
149–156 8C); IR (KBr): n 1260,
3
1 1
7
.02 (t, 2H, J¼8.3 Hz), 7.18 (t, 2H, J¼7.9 Hz), 7.26–7.38
1450, 1715, 3410 (NH) cm2 ; H NMR (400 MHz, CDCl3):
d 6.18 (s, 1H, Ar–CH), 6.87 (s, 2H), 6.92–7.48 (m, 11H),
7.98 (br, s, 2H, NH); Anal. calcd for C H N S: C, 76.80;
(
m, 8H), 7.98 (br, s, 2H, NH); HRMS [Found: m/z
56.1069(M ), calcd for C H ClN M, 356.1080].
þ
3
2
3
17
2:
21 16 2
H, 4.91; N, 8.53. Found: C, 76.62; H, 5.04; N, 8.54.
4
.2.6. (2-Chloro-phenyl)-(1H-indol-3-yl)-methyl]-
1
0a
phenyl-amine, 3f. Pink solid; mp 72–74 8C; IR (KBr): n
010, 1037, 1093, 1337, 1417, 1455, 1616, 3052, 3412
4.2.11. 3k·2AcOEt. Colorless solid; mp 121–123 8C (lit,
138–140 8C); IR (KBr): n 1260, 1450, 1715, 3410
1