C[O:2][C:3]([C:5]1[C:6]2[CH:7]=[N:8][N:9]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[C:10]=2[CH:11]=[C:12]([C:14]#[N:15])[CH:13]=1)=[O:4].[OH-].[Na+].Cl>O.CO>[C:14]([C:12]1[CH:13]=[C:5]([C:3]([OH:4])=[O:2])[C:6]2[CH:7]=[N:8][N:9]([C:16]3[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=3)[C:10]=2[CH:11]=1)#[N:15]To a stirred solution of 6-cyano-1-(4-fluoro-phenyl)-1H-indazole-4-carboxylic acid methyl ester (0.30 g, 1.1 mmol) in water (10 mL) and methanol (10 mL) was added a 2 N aqueous sodium hydroxide (10 mL, 20 mmol). The mixture was warmed at reflux for 1 hour, cooled to room temperature, and acidified with 1 N aqueous HCl (pH=3-4). The white solid was collected by filtration, washed with MeOH (10 mL) and dried to afford 6-cyano-1-(4-fluoro-phenyl)-1H-indazole-4-carboxylic acid.
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