F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12].[CH3:15][N:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1.C(=O)([O-])[O-].[K+].[K+].C(=O)(O)[O-].[Na+]>CN(C)C=O>[CH3:15][N:16]1[CH2:21][CH2:20][N:19]([C:2]2[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][C:3]=2[C:11]([F:14])([F:13])[F:12])[CH2:18][CH2:17]1In 10 mL of dimethylformamide, 300 mg (1.44 mmol) of 2-fluoro-5-nitrobenzotrifluoride was dissolved, and 287 mg (2.88 mmol) of 4-methylpiperazine and 792 mg (5.76 mmol) of potassium carbonate were added thereto and the mixture solution was heated at 70° C. for three hours with vigorous stirring. After cooling, the reaction solution was poured into a saturated sodium bicarbonate solution and extracted with ethyl acetate, and the extract was washed with a saturated sodium chloride solution, and the obtained organic layer as such was used as a substrate in the subsequent catalytic reduction. To the organic layer, 10 mg of 10% palladium carbon was added and the mixture was stirred at room temperature for 16 hours in a hydrogen atmosphere at normal pressures. The catalyst was removed by filtration and the filtrate was concentrated and purified by silica gel column chromatography to obtain 350 mg (94%) of a target product as a brown solid.
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