synthesis and catalytic functionalization of biologically active indoles

3 Publications 96
(q); 115.3 (d, J = 21.2 Hz); 110.8; 109.2; 100.0; 46.8 (CH2); 34.7 (CH2); 29.5; 26.0; 18.2
(q); 9.3; -4.1 ppm. MS (EI, 70 eV) m/z (rel. intensity): 413 (9), 412 (M + , 29), 305 (5), 304
(21), 303 (100), 274 (2), 217 (3), 188 (2), 187 (3), 150 (1), 149 (8). HRMS Calcd. for
C24H33FN2OSi: 412.23407. Found: 412.234775. FTIR (Nujol): 3377, 2928, 2856, 1624,
1588, 1567, 1512, 1489, 1475, 1379, 1281, 1255, 1171, 944, 892, 862, 840, 779 cm -1 .
5-(4-Benzyl-piperazin-1-yl)-3-(tert-butyl-dimethyl-silanyl-oxy)-1,2-dimethyl-1H-indole
(5f)
Yield: 50%. 1 H NMR (300.13, CDCl3): � = 7.40-7.24 (m,
5H); 7.10 (d, 1H, J = 8.8 Hz); 6.97 (d, 1H, J = 2.2 Hz);
6.88 (dd, 1H, J = 8.8 Hz, J = 2.2 Hz); 3.59 (s, 2H); 3.55
(s, 3H); 3.15 (t, 4H, J = 4.9 Hz); 2.67 (t, 4H, J = 4.9 Hz);
2.26 (s, 3H); 1.07 (s, 9H); 0.14 (s, 6H) ppm. 13 C NMR (CDCl3, 75.5 MHz): � = 144.7 (q);
138.0 (q); 130.1 (q); 129.7 (q); 129.3 (2x CH); 128.2 (2x CH); 127.1; 122.9 (q); 121.6 (q);
114.2; 108.8; 104.5; 63.2 (CH2); 53.5 (2x CH2); 51.9 (2x CH2); 29.5; 25.9; 18.2 (q); 9.2; -
4.2 ppm. MS (EI, 70 eV) m/z (rel. intensity): 450 (M +1 , 33), 449 (M + , 100), 435 (7), 434
(19), 358 (15), 304 (16), 303 (67), 302 (16), 245 (9), 217 (8), 92 (6), 91 (29), 77 (10).
HRMS Calcd. for C27H39N3OSi: 449.28569. Found: 449.287064. FTIR (KBr): 3460, 3089,
3023, 2954, 2933, 2860, 2819, 2692, 2214, 1842, 1489, 1464, 1452, 1371, 1296, 1250,
1225, 1175, 1146, 1077, 1005, 953, 889, 839, 808, 788, 779, 739, 700 cm -1 N
OTBDMS
N
CH3 N
CH3 .
[3-(tert-Butyl-dimethyl-silanyloxy)-1,2-dimethyl-1H-indol-5-yl]-morpholin-4-yl-amine
(5h)
Yield: 55%. Mp.: 110-117 °C. 1 H NMR (300.13, CDCl3): � = 7.12
(d, 1H, J = 8.8 Hz); 6.97 (d, 1H, J = 2.3 Hz); 6.86 (dd, 1H, J = 8.8
Hz, J = 2.3 Hz); 3.90 (t, 4H, J = 4.7 Hz); 3.56 (s, 3H); 3.11 (t, 4H, J
= 4.7 Hz); 2.27 (s, 3H); 1.08 (s, 9H); 0.15 (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; 67.5 (CH2); 52.3 (CH2); 29.7; 26.1; 18.4 (q); 9.4; -3.9 ppm. MS (EI, 70 eV) m/z (rel.
intensity): 361 (M +1 , 29), 360 (M + , 100), 303 (7), 302 (8), 245 (5), 86 (2). HRMS Calcd. for
C20H32N2O2Si: 360.22276. Found: 360.222092. FTIR (KBr): 3450, 2957, 2927, 2892,
2851, 2812, 1489, 1459, 1372, 1306, 1292, 1257, 1223, 1164, 1119, 951, 895, 838, 810,
776 cm -1 O
OTBDMS
N
CH3 N
CH3 .