PEG-SO3H AS A CATALYST
2055
136.5, 148.4, 156.9; LCMS (m=z): 410 [M þ H]þ. Anal. calcd. for C27H27N3O: C,
79.19; H, 6.65; N, 10.26. Found C, 79.12; H, 6.59; N, 10.21.
3,3’-((1H-Indol-3-yl)methylene)bis(5-methyl-1H-indole) (5d). Mp: 174–
.
1H NMR (300 MHz,
176 ꢀC, IR (KBr): nmax ¼ 3298, 3010, 2956, 1622 cmꢂ1
DMSO-d6) d: 2.68 (s, 6H), 5.72 (s, 1H, Ar-CH), 6.21 (s, 3H), 6.82 (s, 3H), 7.24–
7.35 (m, 2H), 7.42–7.56 (m, 5H), 10.73 (s, 3H, –NH); LCMS: m=z 390 [M þ H]þ;
13C NMR (DMSO-d6): d 22.4, 54.6, 111.1, 111.8, 112.6, 118.0, 118.8, 119.8, 120.8,
121.7, 123.2, 127.4, 128.5, 128.8, 134.5, 136.5. Anal. calcd. for. C27H23N3: C,
83.26; H, 5.95; N, 10.79. Found: C, 83.18; H, 5.90; N, 10.75.
1,4-Bis(bis(5-bromo-1H-indol-3-yl)methyl)benzene (6b). Mp: 178–180 ꢀC,
IR (KBr): nmax ¼ 3328, 3025, 1632. 1H NMR (300 MHz, DMSO-d6), d (ppm): 5.83 (s,
2H, Ar-CH), 6.55 (s, 4H), 7.21–%32 (m, 4H), 7.26–7.43 (m, 12H), 9.52 (br, s, 4H,
NH); 13C NMR (DMSO-d6): d (ppm): 54.6, 111.4, 113.6, 116.8, 122.0, 123.5,
124.9, 128.8, 129.7, 134.8, 135.7. Anal. calcd. for C40H26Br4N4: C, 54.45; H, 2.97;
N, 6.35. Found: C, 54.39; H, 2.94; N, 6.30.
1,4-Bis(bis(2-methyl-1H-indol-3-yl)methyl)benzene (6c). Mp 188–190 ꢀC,
IR (KBr): nmax ¼ 3342, 2975, 1626. 1H NMR (300 MHz, DMSO-d6), d (ppm): 2.52 (s,
12H), 5.74 (s, 2H, Ar-CH), 6.35 (s, 4H), 7.32–7.39 (m, 4H), 7.45–7.63 (m, 12H), 10.21
(br, s, 4H, NH); 13C NMR (DMSO-d6): d 14.2, 50.6, 112.4, 113.5, 119.2, 120.8, 121.7,
126.3, 128.9, 132.1, 136.5, 137.3. LCMS (m=z): 623 [M þ H]þ. Anal. calcd. for
C44H38N4: C, 84.85; H, 6.15; N, 9.00. Found: C, 84.74; H, 6.08; N, 8.91.
1,4-Bis(bis(5-methyl-1H-indol-3-yl)methyl)benzene (6d). Mp 226–228 ꢀC,
IR (KBr): nmax ¼ 3328, 2986, 1638. 1H NMR (300 MHz, DMSO-d6): d (ppm): 2.56 (s,
12H), 5.72 (s, 2H, Ar-CH), 6.28 (s, 4H), 7.26–7.38 (m, 4H), 7.41–7.66 (m, 12H), 9.18
(br, s, 4H, NH). 13C NMR (DMSO-d6): d 14.1, 51.4, 111.6, 112.8, 117.4, 119.9, 121.2,
126.0, 128.5, 131.4, 135.4, 137.0. LCMS (m=z): 623 [M þ H]þ. Anal. calcd. for
C44H38N4; C, 84.85; H, 6.15; N, 9.00. Found: C, 84.73; H, 6.09; N, 8.94.
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