The mixture was stirred for 45 min, and a solution of 0.001 mol of methyl sulfate in 5 ml of anhydrous DMF CH5424802 concentration was added. Then a few milliliters of water were carefully added to decompose the excess of sodium hydride. The reaction mixture was filtered, the filtrate was cooled, and 20 ml of water was added to it. The precipitation obtained was purified by crystallization

from ethanol and repeated washing with n-hexane. Yield 41 %, mp 71–73 °C. 1H NMR (600 MHz, CDCl3) δ = 7.43 (dd, J = 1.2, 5.3 Hz, 1H, H-para thienyl), 7.21 (d, J = 8.8 Hz, 1H, H-7), 7.15 (dd, J = 3.6, 5.3 Hz, 1H, H-meta thienyl), 7.08 (dd, J = 1.2, 3.6 Hz, 1H, H-ortho thienyl), 7.01 (d, J = 2.4 Hz, 1H, H-4), 6.89 (dd, J = 2.4; 8.8 Hz, 1H, H-6), 3.74 (s, 3H, 5-OMe), 2.25 (s, 3H, 3-Me), 1.24 (s, 3H, 1-Me); 13C NMR (125 MHz, CDCl3) δ = 152.09 (C-5), 132.83 (Cipso thienyl), 131.36 (C-7a), 128.71 (C-2), 122.53(C-ortho thienyl), 123.12 (C-meta thienyl), 123.08 (C-para thienyl), 121.69 (C-3a), 113.18 (C-6), 110.77 (C-3), 110.25 (C-7), 100.73 (C-4), 56.03 (C-5-OMe), 15.42 (N1-Me), 9.61 (C-3-Me); HRMS (EI): m/z 257.3552 C15H15NOS (calcd 257.3553); Anal. Calcd for C15H15NOS: C, 70.01; H, 5.87; N, 5.44; S, 12.46. Found: C, 69.95; H, 5.92; N, 5.48; S, 12.41. find more 1-(1H-Indol-3-yl)-3-phenylprop-2-en-1-one (4) Derivative 4 was obtained by means of Friedel–Crafts acylation according to (Guchhait et al., 2011) in 7.5 % yield as a yellowish white solid; mp 225-230 °C. Spectral data according to (Guchhait et al., 2011). 3-[1-(4-chlorobenzyl)-1H-indol-5-yl]-1-phenylprop-2-en-1-one (5) Yellowish solid (EtOH). This compound was prepared as follows: 0.01 mol of derivative 4 and 30 ml of anhydrous DMF

were mixed in a round-bottomed flask equipped with a thermometer and a dropping funnel. The reaction mixture was cooled to 0 °C and 0.8 g of sodium hydride was added (50 % oil suspension). After 30 min of mixing, a Ureohydrolase solution of 0.012 mol of 4-chlorobenzyl chloride in 20 ml of anhydrous DMF was added dropwise. The reaction was continued at room temperature for 3 h. The mixture was filtered and 10–15 ml of water was added to the filtrate. The resulting resin-like substance was removed and the next portion of water (25–30 ml) was added until the solution becomes opaque. The mixture was kept in refrigeration for two hours and the precipitation obtained was filtered and purified by crystallization from ethanol and repeated washing with n-hexane. Yield 72.0 %, mp 235–238 °C, 1H NMR (600 MHz, CDCl3) δ = 8.64–8.54 (m, 1H, H-5), 7.92 (s, 1H, H-2), 7.85 (d, J = 15.