[Cl-].[Br:2][C:3]1[CH:4]=[CH:5][C:6]2[N:12]([CH2:13][CH:14]=[CH2:15])[CH2:11][CH2:10][C:9]([C:16]([O:18][CH3:19])=[O:17])=[CH:8][C:7]=2[CH:20]=1.CN(C=[O:25])C.O>[Cl-].[Na+].O.[Pd](Cl)Cl>[Br:2][C:3]1[CH:4]=[CH:5][C:6]2[N:12]([CH2:13][C:14](=[O:25])[CH3:15])[CH2:11][CH2:10][C:9]([C:16]([O:18][CH3:19])=[O:17])=[CH:8][C:7]=2[CH:20]=1A mixture of palladium chloride (96 mg) and curious chloride (218 mg) in DMF-water (7-1 ml) was stirred at 60° C. for 18 hours under oxygen atmosphere. To the reaction system was added a solution of methyl 7-bromo-1-(2-propenyl)-2,3-dihydro-1H-1-benzazepine-4-carboxylate (500 mg) in DMF-water (7-1 ml) was added, and the mixture was stirred at 60° C. for 7 hours. To the reaction system was added saturated brine, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried with magnesium sulfate. After concentration under reduced pressure, the residue was separated and purified with column chromatography (ethyl acetate:hexane=1:4→1:2) to give methyl 7-bromo-1-(2-oxopropyl)-2,3-dihydro-1H-1-benzazepine-4-carboxylate (311 mg) as yellow crystals.
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