Sodium hydride → HCID 20135077, compound

Participants

Reaction Steps

To a solution of 7-chloro-1,3,4,5-tetrahydro-3-(methoxycarbonyl)-4-(4-methoxyphenyl)-2H-1-benzazepin-2-one (270 mg; 0.75 mmole; see Example 1C) in dimethylformamide (10 ml), cooled at 0°-5° C. in an ice-water bath, was added 50% sodium hydride (72 mg; 1.5 mmole). After stirring at 0°-5° C. for 15 minutes, methoxymethylbromide (240 μ; 3 mmole) was added dropwise. The reaction mixture was allowed to stir at 0°-5° C. for two additional hours. The excess sodium hydride was destroyed by the addition of water, and the resulting mixture was extracted with ether. The aqueous layer was extracted with ether (three times) and the combined organic layers were dried (magnesium sulfate) and concentrated. The crude residue was flash chromatographed (silica gel/5-20% ethyl acetate:hexane) yielding 233 mg of the title compound as an oil.

Provenance & Evidence