Cesium carbonate → HCID 57625502, compound

Participants

Reaction Steps

A mixture of 1-(1H-indazol-5-yl)-4-(4-(trifluoromethyl)phenyl)pyridin-2(1H)-one (1.1 g, 3.1 mmol), (S)-(+)-glycidyl nosylate (0.96 g, 3.7 mmol) and cesium carbonate (1.5 g, 4.6 mmol) in methyl sulfoxide (10 mL) was stirred at ambient temperature overnight. The reaction mixture was diluted with water (20 mL) and extracted with ethyl acetate (2×50 mL). The combined organic extracts were washed with brine (20 mL), dried (Na2SO4), and concentrated under reduced pressure. Purification by column chromatography (silica gel, ethyl acetate) gave the title compound (510 mg, 40%) as a yellow solid: 1H NMR (500 MHz, CDCl3) δ 8.08 (s, 1H), 7.76-7.73 (m, 5H), 7.64 (d, J=9.0 Hz, 1H), 7.51 (d, J=7.0 Hz, 1H), 7.47 (dd, J=9.0, 2.0 Hz, 1H), 6.92 (d, J=2.0 Hz, 1H), 6.52 (dd, J=7.5, 2.0 Hz, 1H), 4.78 (dd, J=15.5, 3.5 Hz, 1H), 4.48 (dd, J=15.0, 5.5 Hz, 1H), 3.41-3.38 (m, 1H), 2.88 (app t, J=4.5 Hz, 1H), 2.60 (dd, J=5.0, 3.0 Hz, 1H).

Provenance & Evidence