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

Participants

Reaction Conditions

Reaction Steps

To a suspension of sodium hydride (96 mg, 3.99 mmol) in THF (13 mL) at 0° C. was added a solution of N-benzyl-4-(4-chloro-2-fluorophenyl)nicotinamide (680 mg, 1.995 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 (1×5 mL), dried (Na2SO4) and concentrated under reduced pressure to afford crude 6-benzyl-8-chlorobenzo[c][2,7]naphthyridin-5(6H)-one (640 mg, 2.00 mmol, 100%). LC/MS (ESI) m/e 321.0 [(M+H)+, calcd for C19H14ClN2O 321.0]; LC/MS retention time (method A): tR=1.95 min.

Provenance & Evidence