F[CH:2]1[CH:7]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)=O)[CH:6]=[CH:5][CH:4]=[C:3]1[C:16]([F:19])([F:18])[F:17].O.[NH2:21][NH2:22]>CN(C)C1C=CN=CC=1.N1C=CC=CC=1.[Cl-].[Na+].O.CCOC(C)=O>[N:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[C:8]1[NH:21][N:22]=[C:2]2[C:7]=1[CH:6]=[CH:5][CH:4]=[C:3]2[C:16]([F:19])([F:18])[F:17]Next, a solution of (6-fluoro-5-trifluoromethyl-cyclohexa-2,4-dienyl)-pyridin-2-yl-methanone (1.5 g, 5.6 mmol), 4-dimethylaminopyridine (0.5 g) and hydrazine hydrate (5 mL) in pyridine (20 mL) was heated at 100° C. overnight. The reaction mixture was cooled and diluted with brine and EtOAc. The organics were washed with water (3×25 mL), then brine (25 mL) and dried over MgSO4. The reaction mixture was concentrated in vacuo and purified by flash chromatography (silica gel 60, EtOAc/CH2Cl2, 19:1) to afford 3-pyridin-2-yl-7-(trifluoromethyl)-2H-indazole as a pale yellow solid (1.1 g, 76%).
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