[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH:7]1[N:8]=[CH:9][N:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16](OCC)=[O:17])[C:11]=12.O.[OH-].[Na+]>C1COCC1.CCOC(C)=O>[CH:7]1[N:8]=[CH:9][N:10]2[CH:15]=[CH:14][CH:13]=[C:12]([CH2:16][OH:17])[C:11]=12To a cold solution of lithium aluminum hydride (1.62 g, 42.4 mmol, 4.0 eq) in THF (50 mL) was added the crude ethyl imidazo[1,5-a]pyridine-8-carboxylate (2.7 g, 14.2 mmol, 1.0 eq) and the reaction mixture was heated at reflux for 2 h. The reaction was cooled and water (1.7 mL), 15% NaOH (1.7 mL) and water (5.1 mL) were slowly added. Solution was diluted with excess EtOAc and stirred at rt for 30 min. The solution was filtered and the solid was washed with ethyl acetate. Organic layers were combined, dried and solvent was removed to give crude imidazo[1,5-a]pyridine-8-methanol, which was purified by column chromatography (EtOAc/Hexane). MS: exact mass calculated for C8H8N2O, 148.06; m/z found, 149 [M+H]+.
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