Water → HCID 67209758, compound

Participants

Reaction Steps

NaH (23 mg, 0.56 mmol) was added to a stirred solution of 1-methyl-3-phenyl-4-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-6(7H)-one (41 mg, 0.14 mmol) in DMF (4 ml) and the resulting mixture was stirred for 30 min. Then ethyl bromoacetate (47 mg, 6.50 mmol) was added and the mixture was stirred for additional 1 h. To the mixture water (0.5 ml) was added and stirred for 2 h. The reaction mixture was concentrated. 1N aqueous HCL was added to the mixture and the solution was extracted with diethyl ether. The organic layer was washed with water and brine, filtered and dried over anhydrous sodium sulfate. The organic layer was concentrated under reduced pressure. The crude product was purified by flash column chromatography (80% EtOAc in hexane) to yield the title compound (29 mg, 59%) [1H-NMR (CDCl3, 300 MHz) δ 7.45-7.30 (m, 5H), 7.05 (s, 1H), 7.00 (s, 1H), 5.03 (s, 2H), 3.81 (s, 3H); LCMS RtE=1.94 min; [M+H]+=351.0]

Provenance & Evidence