1-Bromo-2-Chloroethane → 1-(1-(2-Chloroethyl)-1H-indazol-5-yl)-4-(4-(trifluoromethyl)phenyl)pyridin-2(1H)-one

Participants

Reaction Steps

To a solution of 1-(1H-indazol-5-yl)-4-(4-(trifluoromethyl)phenyl)pyridin-2(1H)-one (120 mg, 0.338 mmol) in DMSO (2.0 mL) was added 2-bromo-1-chloroethane (485 mg, 3.38 mmol) and Cs2CO3 (330 mg, 1.01 mmol), and the reaction was stirred at ambient temperature for 3 h. The reaction was diluted with H2O (25 mL) and extracted with EtOAc (3×25 mL). The extracts were washed with brine (25 mL), dried over Na2SO4, and concentrated. Flash chromatography (Biotage 25+M column, CH2Cl2/MeOH, 99:1 to 98:2) yielded the title compound (72 mg, 51%): 1H NMR (500 MHz, CDCl3) δ 8.11 (s, 1H), 7.76-7.73 (m, 5H), 7.59-7.47 (m, 3H), 6.92-6.91 (m, 1H), 6.53-6.51 (m, 1H), 4.74-4.71 (m, 2H), 4.00-3.98 (m, 2H).

Provenance & Evidence