Ethanol → HCID 67005920, compound

Participants

Reaction Steps

A mixture of methyl 3-(4-chloro-1-phenyl-1H-pyrazolo[3,4-b]pyridin-5-yl)-2,2-dimethyl-3-phenylpropanoate (27 mg, 0.064 mmol), palladium (10% on carbon, 10 mg), diisopropylethylamine (0.017 mL, 0.096 mmol), and ethanol (3 mL) was stirred under hydrogen balloon for 80 min. The mixture was then filtered through a pad of silica gel and concentrated. The residue was mixed with lithium hydroxide monohydrate (30 mg, 0.7 mmol), water (1 mL), and dioxane (1 mL), and stirred at 110° C. overnight. After cooled, the mixture was partitioned between water and diethyl ether. The ether layer was extracted with water. Combined aqueous solutions were acidified with 10% citric acid aqueous solution and extracted with ethyl acetate. Combined extracts were washed with brine, dried (Na2SO4) and concentrated to give 2,2-dimethyl-3-phenyl-3-(1-phenyl-1H-pyrazolo[3,4-b]pyridin-5-yl)propanoic acid (16 mg, 0.043 mmol, 69% yield).

Provenance & Evidence