[N+:1]([C:4]1[CH:5]=[C:6]([C:14]2[N:15]=[N:16][NH:17][N:18]=2)[CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=1)([O-])=O>CO.[Pd]>[N:18]1[NH:17][N:16]=[N:15][C:14]=1[C:6]1[CH:5]=[C:4]([CH:9]=[C:8]([C:10]([F:11])([F:12])[F:13])[CH:7]=1)[NH2:1]A mixture of 5-(3-nitro-5-(trifluoromethyl)phenyl)-2H-tetrazole (220 mg, 0.849 mmol) in MeOH (10 mL) was added Pd/C (45.2 mg, 0.424 mmol) under N2. The mixture was stirred at 20° C. under a H2 atmosphere for 1 h. LCMS showed the reaction was finished. The mixture was filtrated, and the filtrate was concentrated to give 3-(2H-tetrazol-5-yl)-5-(trifluoromethyl)aniline (200 mg, 0.781 mmol, 92% yield): 1H NMR (400 MHz, METHANOL-d4) δ 7.96 (s, 1H), 7.71 (s, 1H), 7.32 (s, 1H). ES-LCMS (m/z) 230 (M+H).
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