C([O:8][C:9]1[C:14]2[N:15]([CH3:18])[CH:16]=[N:17][C:13]=2[CH:12]=[C:11]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([O:27][CH3:28])[CH:20]=2)[N:10]=1)C1C=CC=CC=1.C([O-])=O.[NH4+].CCO>[OH-].[OH-].[Pd+2].CN(C=O)C>[CH3:28][O:27][C:21]1[CH:20]=[C:19]([C:11]2[N:10]=[C:9]([OH:8])[C:14]3[N:15]([CH3:18])[CH:16]=[N:17][C:13]=3[CH:12]=2)[CH:24]=[CH:23][C:22]=1[O:25][CH3:26]To a mixture of 4-(benzyloxy)-6-(3,4-dimethoxyphenyl)-3-methyl-3H-imidazo[4,5-c]pyridine 2.26 (290 mg, 0.772 mmol), Pd(OH)2 (46 mg, 60 mg/mmol), and ammonium formate (975 mg, 15.5 mmol) under N2 was added EtOH (12 mL) and DMF (4 mL) and the mixture was heated to 75° C. for 30 minutes. The reaction was cooled, filtered through celite and washed with EtOH/DCM. The filtrate was concentrated, dry loaded onto a column, and purified by flash chromatography (EtOAc→10% MeOH/EtOAc) to afford 6-(3,4-dimethoxyphenyl)-3-methyl-3H-imidazo[4,5-c]pyridin-4-ol 2.27.
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