Water → HCID 23091725, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 4-[(5-bromo-3-formylpyridin-2-yl)(isobutyl)amino]butanoate (750 mg) in dimethyl carbonate (20 ml) was added a 28% sodium methoxide solution in methanol (810 mg), and the mixture was heated at 50° C. for 2 hours under a nitrogen atmosphere. The mixture was returned to room temperature, water was added thereto and then extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=19:1→hexane:ethyl acetate=6:1) to give methyl 3-bromo-9-isobutyl-8,9-dihydro-7H-pyrido[2,3-b]azepine-6-carboxylate (654 mg) as a yellow oily material.

Provenance & Evidence