synthesis and catalytic functionalization of biologically active indoles

3 Publications 95
456.258767. FTIR (Nujol): 3379, 2925, 2854, 1668, 1626, 1565, 1461, 1378, 1263, 1168,
1074, 948, 891, 839, 787, 701cm -1 .
[3-(tert-Butyl-dimethyl-silanyloxy)-1,2-dimethyl-1H-indol-5-yl]-phenyl-amine (5c)
Yield: 85%. Mp: 135-140 °C. 1 H NMR (300.13, CDCl3): � = 7.24
(d, 1H, J = 1.9 Hz); 7.21-7.11 (m, 3H); 6.95-6.87 (m, 3H); 6.78
(m, 1H); 3.59 (s, 3H); 2.29 (s, 3H); 1.58 (bs, 1H, NH); 1.05 (s,
9H) ppm. 13 C NMR (CDCl3, 75.5 MHz): � = 146.9 (q); 133.7 (q); 131.2 (q); 130.4 (q); 129.4
(2xCH); 123.7 (q); 122.2 (q); 118.8; 117.2; 115.0 (2xCH); 110.7; 109.2; 29.8; 26.1; 18.4 (q);
9.5; -4.0 ppm. MS (EI, 70 eV) m/z (rel. intensity): 367 (M +1 , 30), 366 (M + , 100), 310 (6),
309 (9), 236 (9), 235 (7), 167 (4), 73 (11). HRMS Calcd. for C22H39N2OSi: 366.21219.
Found: 366.211482. FTIR (Nujol): 3384, 2925, 2854, 1600, 1511, 1462, 1376, 1321, 1250,
1156, 1072, 938, 895, 842, 801, 782, 741, 690 cm -1 H OTBDMS
N
CH3 N
CH3 .
[3-(tert-Butyl-dimethyl-silanyloxy)-1,2-dimethyl-1H-indol-5-yl]-phenethyl-amine (5d)
Yield: 60%. Mp: 77-80 °C. 1 H NMR (300.13, CDCl3): � =
7.31 (m, 2H); 7.22 (m, 3H); 7.01 (d, 1H, J = 8.6 Hz); 6.71
(d, 1H, J = 2.2 Hz); 6.52 (dd, 1H, J = 8.6 Hz, J = 2.2 Hz);
3.53 (s, 3H); 3.43 (t, 2H, J = 6.8 Hz); 2.94 (t, 2H, J = 6.8
Hz); 2.25 (s, 3H); 1.07 (s, 9H); 0.15 (s, 6H) ppm. 13 C NMR (CDCl3, 75.5 MHz): � = 140.9
(q); 140.0 (q); 129.9 (q); 129.1 (2x CH); 129.0 (q); 128.8 (2x CH); 126.5; 123.1 (q); 122.4
(q); 111.1; 109.3; 100.3; 46.9 (CH2); 35.8 (CH2); 29.8; 26.2; 18.5 (q); 9.5; -3.9 ppm. MS
(EI, 70 eV) m/z (rel. intensity): 395 (M +1 , 16), 394 (M + , 60), 303 (100), 302 (6), 264 (4), 263
(1), 174 (3), 173 (17), 142 (11), 141 (11), 73 (7). HRMS Calcd. for C24H34N2OSi:
394.24349. Found: 394.243114. FTIR (Nujol): 3348, 2927, 2855, 1620, 1581, 1493, 1467,
1377, 1286, 1250, 1163, 941, 891, 874, 840, 778, 741, 700,cm -1 H OTBDMS
N
CH3 N
CH3 .
[3-(tert-Butyl-dimethyl-silanyloxy)-1,2-dimethyl-1H-indol-5-yl]-[2-(4-fluoro-phenyl)ethyl]-amine
(5e)
Yield: 91%. 1 H NMR (300.13, CDCl3): � = 7.22-7.18 (m,
2H); 7.06-6.98 (m, 3H); 6.72 (d, 1H, J = 2.1 Hz); 6.53 (dd,
1H, J = 8.7 Hz, J = 2.1 Hz); 3.56 (s, 3H); 3.43 (t, 2H, J =
6.9 Hz); 2.93 (t, 2H, J = 6.9 Hz); 2.28 (s, 3H); 1.09 (s,
9H); 0.18 (s, 6H) ppm. 13 H OTBDMS
N
CH3 F
N
CH3 C NMR (CDCl3, 75.5 MHz): � = 161.6 (d, J = 244 Hz, q); 140.6
(q); 135.4 (d, J = 3.2 Hz, q); 130.3 (d, J = 7.8 Hz); 129.7 (q); 128.8 (q); 123.1 (q); 122.2