Iodine → HCID 178452208, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of tert-butyl 4-(5-phenyl-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate (3 g, 7.75 mmol) and powdered potassium hydroxide (1.28 g, 19.4 mmol) in DMF (20 mL) was treated with iodine (3.93 g, 15.5 mmol), and the mixture was heated at 60° C. After 4 hours, the mixture was cooled to room temperature and treated with powdered KOH (700 mg, 10.7 mmol) and I2 (1.97 g, 7.75 mmol). The mixture was stirred at 60° C. for 1 hour. The mixture was cooled to room temperature, diluted with EtOAc (200 mL) and successively washed with saturated Na2S2O3 solution (2×20 mL) and water (2×50 mL). The organic layer was separated, dried (MgSO4), filtered, and concentrated in vacuo. The residue obtained was crystallized from boiling CH3CN to provide tert-butyl 4-(3-iodo-5-phenyl-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate (3.12 g, 79.7% yield) as a solid. LCMS (APCI+) m/z 506 (M+H)+, Retention time=4.04 minutes.

Provenance & Evidence