Sodium hydride → 7-bromo-6-fluoro-2-(4-methoxybenzyl)isoquinolin-1(2H)-one

Participants

Reaction Steps

9.66 g (39.9 mmol) of 7-bromo-6-fluoro-2H-isoquinolin-1-one (312) were dissolved in 180 mL of dimethyl acetamide and 1.92 g (48.0 mmol) of sodium hydride (60%) were added. After 1 h at room temperature a solution of 7.50 g (48.0 mmol) of 4-methoxy benzylchloride in 25 mL of dimethyl acetamide was added. The mixture was stirred at room temperature until complete conversion is achieved. For the isolation procedure, the solvent is removed i. vac., the residue was taken up in saturated sodium bicarbonate solution and extracted three times with dichloromethane. The organic layers are dried with MgSO4 and evaporated to yield 16.8 g of a dark oil as crude product, which was stirred in methanol. Filtration of the precipitate gave 6.56 g of the title compound as a yellow solid. The mother liquor was evaporated and the residue purified by preparative HPLC, which gave additional 2.62 g of the desired product. Rt=1.71 min (Method C). Detected mass: 362.3/364.3 (M+H+).

Provenance & Evidence