5-chloro-N-methoxy-8-[(2R)-2-(methoxymethyl)pyrrolidin-1-yl]-N-methylquinoline-7-carboxamide → 1-{5-chloro-8-[(2R)-2-(methoxymethyl)pyrrolidin-1-yl]quinolin-7-yl}ethanone

Participants

Reaction Steps

To a mixture of 5-chloro-N-methoxy-8-[(2R)-2-(methoxymethyl)pyrrolidin-1-yl]-N-methylquinoline-7-carboxamide (132 mg, 0.363 mmol) in tetrahydrofuran (0.5 mL) was added 1.40 M methylmagnesium bromide in tetrahydrofuran (1.6 mL, 2.2 mmol). The reaction was stirred at room temperature overnight, quenched with saturated ammonium chloride, and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, then concentrated to dryness under reduced pressure. The resultant residue was purified on silica gel, eluting with 0 to 10% methanol in dichloromethane, to give the desired product (14 mg, 12%). LCMS calculated for C17H20ClN2O2(M+H)+: m/z=319.1; found: 319.1.

Provenance & Evidence