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

Participants

Reaction Conditions

Reaction Steps

To a suspension of sodium hydride (79 mg, 3.28 mmol) in THF (8 mL) at 0° C. was added a solution of 4-(4-chloro-2-fluorophenyl)-N-isopropylnicotinamide (480 mg, 1.640 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 an additional 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 8-chloro-6-isopropylbenzo[c][2,7]naphthyridin-5(6H)-one (250 mg, 0.917 mmol, 56% yield). LC/MS (ESI) m/e 273.0 [(M+H)+, calcd for C15H14ClN2O 273.1]; LC/MS retention time (method C): tR=1.98 min; 1H NMR (400 MHz, CDCl3) δ ppm 9.67 (s, 1H), 8.70 (d, J=6.0 Hz, 1H), 8.17-8.19 (d, J=8.4 Hz, 1H), 7.92-7.94 (d, J=5.6 Hz, 1H), 7.62 (d, J=1.6 Hz, 1H), 7.26-7.31 (dd, J=8.8, 2.0 Hz, 1H), 3.21-3.28 (m, 1H), 1.71 (d, J=6.8 Hz, 6H).

Provenance & Evidence