[CH3:1][O:2][C:3]1[C:4]2[N:5]([N:15]=[CH:16][C:17]=2[CH:18]=[O:19])[CH:6]=[C:7]([C:9]2[CH:10]=[N:11][N:12]([CH3:14])[CH:13]=2)[CH:8]=1.P([O-])(O)(O)=[O:21].[Na+].CC(=CC)C.Cl([O-])=O.[Na+]>O.C(OCC)(=O)C.C(O)CCC>[CH3:1][O:2][C:3]1[C:4]2[N:5]([N:15]=[CH:16][C:17]=2[C:18]([OH:21])=[O:19])[CH:6]=[C:7]([C:9]2[CH:10]=[N:11][N:12]([CH3:14])[CH:13]=2)[CH:8]=1To a suspension of 4-methoxy-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridine-3-carbaldehyde (25.0 mg, 0.098 mmol) in water (1 ml) was added sodium dihydrogen phosphate (82 mg, 0.68 mmol). After 5 minutes, n-butanol (5 ml), 2-methyl-2-butene (0.145 ml, 1.37 mmol), and sodium chlorite (79 mg, 0.88 mmol) were added. After 3 hours, LCMS indicated incomplete conversion to product. Sodium chlorite (44 mg, 0.49 mmol) and 2-methyl-2-butene (0.104 ml, 0.98 mmol) were added. After 16 hours, reaction mixture was diluted with ethyl acetate, washed with water and brine, then dried over magnesium sulfate, filtered, and concentrated to give 4-methoxy-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridine-3-carboxylic acid as white solids which were used without further purification. LRMS (ESI) calculated for C13H13N4O3 [M+H]+, 273.1 found 273.0.
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