[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[C:11]([NH:13][CH:14]=O)[CH:10]=[N:9]2)=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1.[OH-].[NH4+].CO.C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH:12]=[C:11]([NH:13][CH3:14])[CH:10]=[N:9]2)=[CH:6][CH:7]=1A mixture of N-[1-(4-fluorophenyl)pyrazol-4-yl]formamide (0.275 g, 1.33 mmol) and LiAlH4 (1.33 mL, 2.66 mmol, 2 M in THF) in THF (5 mL) was heated at 45° C. for 1 h. The reaction mixture was cooled to room temperature and diluted with 5 mL of concentrated ammonium hydroxide and 80 mL of 20% MeOH/CH2Cl2. The organic layer was separated, dried over anhydrous sodium sulfate, filtered, concentrated in vacuo, and purified by flash chromatography (SiO2, 0-100% EtOAc/CH2Cl2 gradient elution) to give 1-(4-fluorophenyl)-N-methylpyrazol-4-amine as an oil (0.23 g, 90%).
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