[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][CH:16]=2)[C:10]=1[C:11]([F:14])([F:13])[F:12])=[O:5])[CH3:2].C([O-])=O.[NH4+]>CO.[Pd]>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([C:15]2[CH:16]=[CH:17][C:18]([NH2:21])=[CH:19][CH:20]=2)[C:10]=1[C:11]([F:14])([F:13])[F:12])=[O:5])[CH3:2]To 1-(4-nitrophenyl)-5-trifluoromethyl-1H-pyrazole-4-carboxylic acid ethyl ester (0.5 g, 1.5 mmol) dissolved in methanol (4 mL) was added palladium on carbon and ammonium formate (0.428 g, 6.8 mmol). This mixture was stirred at room temperature overnight. The solvent was removed under vacuum, then the material was resuspended in chloroform, and washed with water (twice) and saturated sodium bicarbonate (once), and the organic layer dried over magnesium sulfate (MgSO4). The solid was filtered and the solvents removed under vacuum. The reaction product was purified over silica gel to yield the named product (m.p. 102° C.–103° C.).
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