Sodium hydride → N-(5-Bromopyridin-3-yl)-5,7-difluoro-3-methyl-2-(4-methylpyridin-2-yl)-quinolin-4-amine

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Reaction Steps

A screwcap vial was charged with a solution of 5-bromopyridin-3-amine (273 mg, 1.58 mmol) in dry DMF (8 mL) under nitrogen. To this stirring solution was slowly added sodium hydride (63.0 mg, 1.58 mmol), followed 5 min later by 4-chloro-5,7-difluoro-3-methyl-2-(4-methylpyridin-2-yl)quinoline (400 mg, 1.31 mmol). The reaction mixture was then stirred at rt for 6 h. Additional portions of sodium hydride (1.2 equivalents) were added after 2 and 4 h of stirring. Upon completion, the reaction was quenched with 10% aq. sodium carbonate and the product was extracted with EtOAc. The organic layer was washed with brine, dried over magnesium sulfate, and cond. The resulting crude residue was purified by flash-chromatography (silica gel, 0-60% EtOAc in hexanes) and subsequently by recrystallization in MeOH. This afforded N-(5-bromopyridin-3-yl)-5,7-difluoro-3-methyl-2-(4-methylpyridin-2-yl)quinolin-4-amine. Mass Spectrum (ESI) m/e=441.0 (M+1).

Provenance & Evidence