C([O:3][C:4]([C:6]1[C:7]2[N:8]([C:12]([C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)=[N:13][CH:14]=2)[CH:9]=[CH:10][CH:11]=1)=[O:5])C.[OH-].[K+]>CO.O>[F:21][C:18]1[CH:17]=[CH:16][C:15]([C:12]2[N:8]3[CH:9]=[CH:10][CH:11]=[C:6]([C:4]([OH:5])=[O:3])[C:7]3=[CH:14][N:13]=2)=[CH:20][CH:19]=1To a solution of 3-(4-fluorophenyl)-imidazo[1,5-a]pyridine-8-carboxylic acid ethyl ester (290 mg, 1.0 mmol) in methanol (20 mL) is added a solution of 85% potassium hydroxide pellets (0.300 g, 3.92 mmol) in water (5.0 mL). The reaction mixture is warmed at reflux for 5 minutes, cooled to room temperature and concentrated in vacuo to remove excess methanol. The mixture is acidified to pH 4 with 1 N aqueous HCl and the resulting precipitate is collected by filtration, washed with water and dried to afford the title product.
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