Sodium hydride → HCID 86710344, compound

Participants

Reaction Steps

To a stirred solution of 4-amino-8-chloro-6-methylbenzo[c][2,7]naphthyridin-5(6H)-one (30 mg, 0.059 mmol) in DMF (10 mL) at 0° C. was added NaH (7.09 mg, 0.295 mmol) and the reaction was stirred for 5 min. To this mixture, 1-(chloromethyl)-4-methoxybenzene (0.026 mL, 0.191 mmol) was added and stirred at rt for 16 h. The reaction was quenched by addition of ice and the reaction mixture extracted with ethyl acetate (2×10 mL). The combined organic layers were washed with water (25 mL), dried over sodium sulfate, and concentrated under reduced pressure to yield 8-chloro-4-((4-methoxybenzyl)amino)-6-methylbenzo[c][2,7]naphthyridin-5(6H)-one (29 mg, 0.044 mmol, 75% yield). LC/MS (ESI) m/e 380.27 [(M+H)+, calcd for C21H19ClN3O2380.11]; LC/MS retention time (Method D): tR=0.86 min.

Provenance & Evidence