Sodium hydride → HCID 86710330, compound

Participants

Reaction Steps

To a suspension of sodium hydride (56.6 mg, 1.42 mmol) in THF (5 mL) at 0° C. was slowly added 4-(4-chloro-2,5-difluorophenyl)-N-methylnicotinamide (100 mg, 0.354 mmol) in THF (5 mL). The resultant mixture was stirred at room temperature for 1 h. The reaction was then quenched by addition of cold water (1 mL) and extracted with ethyl acetate (2×2 mL). The combined organic extracts were dried with sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography (1:1 ethyl acetate in petroleum ether) to afford 8-chloro-9-fluoro-6-methylbenzo[c][2,7]naphthyridin-5(6H)-one (82 mg, 0.297 mmol, 84% yield) as white solid. LC/MS (ESI) m/e 262.5 [(M+H)+, calcd for C13H9ClFN2O 263.0]; LC/MS retention time (method D): tR=1.79 min; HPLC retention time (method A): tR=7.35 min; HPLC retention time (method B): tR=7.07 min.

Provenance & Evidence