5-Chloro-7-{[methoxy(methyl)amino]carbonyl}quinolin-8-yl trifluoromethanesulfonate → 1-[5-Chloro-8-(3-fluorophenyl)quinolin-7-yl]ethanone

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Reaction Steps

To a mixture of 5-chloro-8-(3-fluorophenyl)-N-methoxy-N-methylquinoline-7-carboxamide (154 mg, 0.447 mmol) and 5-chloro-7-{[methoxy(methyl)amino]carbonyl}quinolin-8-yl trifluoromethanesulfonate (154 mg, 0.386 mmol) in tetrahydrofuran (1 mL) was added 1.40 M methylmagnesium bromide in tetrahydrofuran (3.8 mL, 5.3 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, and then concentrated to dryness under reduced pressure. The resultant residue was purified on silica gel, eluting with 0 to 50% of EtOAc in hexane, to give the desired product (38 mg, 32%). LCMS calculated for C17H12ClFNO(M+H)+: m/z=300.1; found: 300.0.

Provenance & Evidence