[F:1][C:2]1[C:10]([N+:11]([O-])=O)=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([CH3:16])([CH3:15])[C:5](=[O:14])[NH:6]2.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH:24]([CH3:26])[CH3:25].[Cl-].[NH4+]>CN(C=O)C>[NH2:11][C:10]1[C:2]([F:1])=[C:3]2[C:7](=[CH:8][CH:9]=1)[N:6]([CH:24]([CH3:26])[CH3:25])[C:5](=[O:14])[C:4]2([CH3:16])[CH3:15]To a solution of 4-fluoro-3,3-dimethyl-5-nitro-1,3-dihydro-2H-indol-2-one (500 mg) and cesium carbonate (1.82 g) in DMF (10 mL) was added dropwise 2-bromopropane (0.523 mL) at room temperature, and the mixture was stirred at 80° C. for 2 hr under a nitrogen atmosphere. To the reaction mixture was added saturated aqueous ammonium chloride solution at 0° C., and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was dissolved in ethanol (10 mL), palladium on carbon (containing water (50%), 237 mg) was added thereto, and the mixture was stirred at room temperature for 2 hr under a hydrogen atmosphere. The palladium on carbon was removed by filtration, and the filtrate was concentrated under reduced pressure to give the title compound (330 mg).
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