Sodium hydride → HCID 178503206, compound

Participants

Reaction Steps

cis-N-[4-(4-Chloro-pentoylamino)-cyclohexyl]-5-fluoro-2-(3-methylsulfanyl-phenoxy)-nicotinamide (259 mg, 0.486 mmol) was dissolved in N-methylpyrrolidine (5 ml) under nitrogen at room temperature and sodium hydride (60% dispersion in mineral oil, 49 mg, 1.21 mmol) was added. The reaction was stirred at room temperature for 18 h and quenched with water (10 ml) then extracted with ethyl acetate (5×10 ml). The combined organic extracts were washed with water (3×5 ml), brine (5 ml), dried over MgSO4 and the solvent was removed under reduced pressure. The residue was purified by flash column chromatography on silica gel eluting with dichloromethane:methanol (97:3, by volume) and the product was triturated with diethylether (2 ml) to give 5-Fluoro-2-(3-methylsulfanyl-phenoxy)-N-[cis-4-(2-oxo-piperidin-1-yl)-cyclohexyl]-nicotinamide (69 mg) as a white solid.

Provenance & Evidence