1
1608.16 (C=N) cm-1; H NMR (400 MHz, DMSO-d6) δ (ppm): 2.35 (s, 3H, CH3),
3.78 (s, 3H, OCH3), 4.54 (s, 2H, CH2), 6.75 (d, J = 8.9 Hz, 1H, CHarom.), 6.97 (d, J =
9.0 Hz, 1H, CHarom.), 7.15 (s, 1H, CHarom.), 7.60-7.65 (m, 4H, CHarom.), 7.71 (d, J = 8.3
Hz, 2H, CHarom.), 7.99 (d, J = 8.3 Hz, 2H, CHarom.); 13CNMR (100 MHz, DMSO-d6) δ
(ppm): 13.46, 21.94, 56.07, 102.33, 112.20, 112.32, 115.13, 125.62, 129.25, 129.55,
129.83, 130.47, 130.98, 131.63, 134.51, 136.41, 136.79, 138.36, 156.32, 167.56,
168.40, 179.03. Elemental Analysis Calcd. (%) for C26H19Cl2N3O3 (492.35): C, 63.43;
H, 3.89; N, 8.53. Found: C, 63.36; H, 3.69; N, 8.47.
5.2.3. 1-(4-Chlorobenzoyl)-2-methyl-5-methoxy-3-{[3-(4-methoxyphenyl)-1,2,4-
oxadiazol-5-yl]-methyl}-1H-indole (5c)
Yield 82 %; pale beige solid; m.p.: 146-147 °C. IR (ATR) max 3075.13 (CH
aromatic), 2994.19, 2940.22, 2901.27, 2835.43 (CH aliphatic), 1672.41 (C=O
benzoyl), 1612.76 (C=N) cm-1; 1H NMR (400 MHz, DMSO-d6) δ (ppm): 2.34 (s, 3H,
CH3), 3.76 (s, 3H, OCH3), 3.83 (s, 3H, OCH3), 4.53 (s, 2H, CH2), 6.75 (d, J = 9.0 Hz,
1H, CHarom.), 6.95 (d, J = 9.0 Hz, 1H, CHarom.), 7.09 (d, J = 8.6 Hz, 2H, CHarom.), 7.16
(s, 1H, CHarom.), 7.65 (d, J = 8.4 Hz, 2H, CHarom.), 7.71 (d, J = 8.3 Hz, 2H, CHarom.),
13
7.92 (d, J = 8.6 Hz, 2H, CHarom.); CNMR (100 MHz, DMSO-d6) δ (ppm): 13.60,
21.83, 55.87, 55.93, 102.12, 112.11, 112.50, 115.14, 118.93, 129.13, 129.55, 130.47,
130.79, 131.71, 134.45, 136.34, 138.27, 156.15, 162.20, 167.93, 168.38, 178.44.
Elemental Analysis Calcd. (%) for C27H22ClN3O4 (487.93): C, 66.46; H, 4.54; N,
8.61. Found: C, 66.40; H, 4.36; N, 8.57.
5.2.4. 1-(4-Chlorobenzoyl)-2-methyl-5-methoxy-3-{[3-(3,4-dimethoxyphenyl)-1,2,4-
oxadiazol-5-yl]-methyl}-1H-indole (5d)
Yield 81 %; white solid; m.p.: 176-178 °C. IR (ATR) max 3065.23 (CH aromatic),
2972.06, 2942.37, 2902.48, 2855.25 (CH aliphatic), 1675.13 (C=O benzoyl), 1593.53
(C=N) cm-1; 1H NMR (400 MHz, DMSO-d6) δ (ppm): 2.35 (s, 3H, CH3), 3.77 (s, 3H,
OCH3), 3.83 (s, 6H, 2OCH3), 4.53 (s, 2H, CH2), 6.75 (d, J = 8.9 Hz, 1H, CHarom.),
6.95 (d, J = 8.9 Hz, 1H, CHarom.), 7.12 (d, J = 8.3 Hz, 1H, CHarom.), 7.17 (s, 1H,
CHarom.), 7.47 (s, 1H, CHarom.), 7.57 (d, J = 8.3 Hz, 1H, CHarom.), 7.65 (d, J = 7.8 Hz,
2H, CHarom.), 7.71 (d, J = 7.9 Hz, 2H, CHarom.); 13CNMR (100 MHz, DMSO-d6) δ
(ppm): 13.60, 21.88, 55.93, 56.13 (2 OCH3), 102.12, 110.21, 112.14, 112.50, 115.20,
118.96, 120.97, 129.55, 130.45, 130.80, 131.71, 134.45, 136.33, 138.27, 149.55,
152.03, 156.16, 168.07, 168.39, 178.42. Elemental Analysis Calcd. (%) for
26