Ethyl 3-oxo-2-phenylpropanoate → 1-tert-Butyl-3-cyclobutyl-5-phenyl-1,7-dihydro-pyrazolo[3,4-b]pyridin-6-one

Participants

Reaction Conditions

Reaction Steps

To a stirring solution of crude 2-tert-butyl-5-cyclobutyl-2H-pyrazol-3-ylamine (1.0 g, 5.2 mmol) in AcOH (5 mL) was added 3-oxo-2-phenyl-propionic acid ethyl ester (1.0 g, 5.2 mmol). The reaction was then heated to 110° C. for 18 hr, at which time the reaction was cooled to room temperature, concentrated under reduced pressure to remove HOAc, diluted with EtOAc, and quenched with a saturated aqueous solution of NaHCO3. The organic layer was dried over MgSO4, filtered through a fritted funnel, and concentrated under reduced pressure. Purification of the resulting material was accomplished by flash chromatography with a Biotage® 35L column (A Dynax Corp., Charlottesville, Va.), eluting with a gradient of 5%, 10%, 20% EtOAc/hexanes. The product was collected and concentrated under reduced pressure to give the title compound (15 mg, 9% yield). LRMS m/z (APCl) 322 (M+1).

Provenance & Evidence