synthesis and catalytic functionalization of biologically active indoles

3 Publications 97
3-(tert-Butyl-dimethyl-silanyloxy)-1,2-dimethyl-5-pyrrolidin-1-yl-1H-indole (5i)
Yield: 73%. Mp: 150-155 °C. 1 H NMR (300.13, CDCl3): � = 7.23 (d,
1H, J = 8.6 Hz); 6.70-6.50 (m, 2H); 3.55 (s, 3H); 3.31 (t, 4H, J = 6.2
Hz); 2.27 (s, 3H); 2.03 (t, 4H, J = 6.2 Hz); 1.09 (s, 9H); 0.17 (s,
6H)ppm. 13 C NMR (CDCl3, 75.5 MHz): 144.8 (q); 130.3 (q); 130.0
(q); 123.3 (q); 121.9 (q); 113.8; 109.1; 104.5; 48.9 (CH2)2; 29.8; 26.1; 25.5 (CH2)2; 18.4 (q);
9.5; -3.9 ppm. MS (EI, 70 eV) m/z (rel. intensity): 344 (M + , 100), 287 (8), 229 (5), 73 (9).
HRMS Calcd. for C20H32N2OSi: 344.22784. Found: 344.227392. FTIR (KBr): 3433, 3078,
2954, 2927, 2893, 2856, 1806, 1626, 1498, 1480, 1376, 1356, 1314, 1302, 1286, 1250,
1175, 906, 897, 838, 777 cm -1 OTBDMS
N
CH3 N
CH3 .
[3-(tert-Butyl-dimethyl-silanyloxy)-1,2-dimethyl-1H-indol-5-yl]-hexyl-amine (5j)
Yield: 95%. Mp.: 83-90°C. 1 H NMR (300.13, CDCl3): � =
7.01 (d, 1H, J = 8.4 Hz); 6.67 (d, 1H, J = 2.2 Hz); 6.54 (dd,
1H, J = 2.2 Hz, J = 8.4 Hz); 3.53 (s, 3H); 3.13 (t, 2H, J =
7.1 Hz); 2.25 (s, 3H); 1.70-1.58 (m, 2H); 1.50-1.20 (m,
6H); 1.1 (s, 9H); 0.92 (t, 3H, J = 6.7 Hz); 0.17 (s, 6H) ppm. 13 C NMR (CDCl3, 75.5 MHz): �
= 141.6 (q); 129.9 (q); 128.9 (q); 123.0 (q); 122.4 (q); 110.9; 109.2; 99.8; 46.0 (CH2); 32.0
(CH2); 29.9 (CH2); 29.7; 27.2 (CH2); 26.1; 22.9 (CH2); 18.4 (q); 14.3; 9.4; -3.9 ppm. MS
(EI, 70 eV) m/z (rel. intensity): 375 (M +1 , 28), 374 (M + , 100), 304 (13), 303 (57), 245 (3),
244 (8), 173 (18), 142 (7), 84 (10). HRMS Calcd. for C22H38N2OSi: 374.27479. Found:
374.274037. FTIR (Nujol): 3395, 2927, 2856, 1624, 1568, 1463, 1378, 1282, 1246, 1168,
1069, 1006, 939, 895, 841, 778, 728 cm -1 H OTBDMS
N
CH3 N
CH3 .