Water → Bms-777607

Participants

Reaction Steps

To 3-chloro-4-(4-(4-ethoxy-1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxamido)-2-fluorophenoxy)picolinamide (1.2 g, 2.1 mmol) in ethyl acetate (16 mL), acetonitrile (16 mL), and water (8 mL) at 0° C. was added iodobenzene diacetate (820 mg, 2.6 mmol, Aldrich). After stirring at rt for 2 h, the reaction was filtered to collect the crude product. The solid was washed with additional ethyl acetate. The filtrate was washed with saturated aqueous sodium bicarbonate solution and the organic phase was dried over anhydrous sodium sulfate and concentrated in vacuo. The precipitate and filtrate were combined and purified by flash chromatography on silica gel (2% methanol/chloroform) to give the title compound (810 mg, 74%) as a white solid. 1H NMR (DMSO-d6) δ 10.57 (s, 1H), 7.83-7.79 (m, 2H), 7.67 (d, 1H, J=5.6 Hz), 7.41-7.38 (m, 3H), 7.36-7.22 (m, 3H), 6.44 (d, 1H, J=7.6 Hz), 6.36 (br s, 2H), 5.86 (d, 1H, J=6.0 Hz), 4.18 (q, 2H, J=7.2 Hz), 1.23 (t, 3H, J=7.2 Hz); MS(ESI+) m/z 513.09 (M+H)+.

Provenance & Evidence