Sodium hydride → 8-chloro-6-cyclopropylbenzo[c][2,7]naphthyridin-5(6H)-one

Participants

Reaction Conditions

Reaction Steps

To a suspension of sodium hydride (72.6 mg, 3.03 mmol) in THF (8 mL) at 0° C. was added a solution of 4-(4-chloro-2-fluorophenyl)-N-cyclopropylnicotinamide (440 mg, 1.51 mmol) in THF (10 mL) dropwise over a period of 10 min. The reaction mixture was stirred at 0° C. for 1 h and then warmed to room temperature and stirred for another 1 h. The reaction mixture was then treated with ice and extracted with ethyl acetate (3×5 mL). The combined organic layers were washed with brine (2×5 mL), dried (Na2SO4) and concentrated under reduced pressure to afford crude 8-chloro-6-cyclopropylbenzo[c][2,7]naphthyridin-5(6H)-one (340 mg, 1.26 mmol, 83% yield) as an off-white solid. LC/MS (ESI) m/e 271.0 [(M+H)+, calcd for C15H12ClN2O 271.1]; LC/MS retention time (method C): tR=1.89 min.

Provenance & Evidence