[F:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([CH3:16])([CH3:15])[C:5](=[O:14])[NH:6]2.[H-].[Na+].Br[CH2:20][CH:21]1[CH2:23][CH2:22]1.[Cl-].[NH4+]>CN(C=O)C>[CH:21]1([CH2:20][N:6]2[C:7]3[C:3](=[C:2]([F:1])[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=3)[C:4]([CH3:16])([CH3:15])[C:5]2=[O:14])[CH2:23][CH2:22]1To a solution of 4-fluoro-3,3-dimethyl-5-nitro-1,3-dihydro-2H-indol-2-one (300 mg) in DMF (10 mL) were added sodium hydride (69.6 mg) and (bromomethyl)cyclopropane (0.193 mL) at 0° C., and the mixture was allowed to be warmed to room temperature, and stirred overnight under a nitrogen atmosphere. The reaction mixture was cooled to 0° C., saturated aqueous ammonium chloride solution was added thereto, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (317 mg).
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