[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][CH2:10][CH2:9][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:7][C:6]=2[CH:16]=1.[H-].[Na+].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.O>CN(C=O)C>[CH2:19]([N:11]1[C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:16][C:6]=2[CH:7]=[C:8]([C:12]([O:14][CH3:15])=[O:13])[CH2:9][CH2:10]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1In DMF (3 ml) was dissolved methyl 7-bromo-2,3-dihydro-1H-1-benzazepine-4-carboxylate (0.3 g), and the solution was added dropwise to a suspension of 60% sodium hydride (0.05 g) in DMF (1 ml) under ice-cooling. The mixture was stirred under nitrogen atmosphere for 10 minutes. Benzyl bromide (0.15 ml) was added thereto, and the mixture was heated at 45° C. for 4 hours. The mixture was poured into water, and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried with anhydrous magnesium sulfate. The solvent was evaporated and the residue was purified with silica gel column chromatography (ethyl acetate/hexane) to give methyl 1-benzyl-7-bromo-2,3-dihydro-1H-1-benzazepine-4-carboxylate (0.3 g) as yellow oil.
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