Iodine → HCID 178452208, compound

Participants

Reaction Conditions

Reaction Steps

I2 (0.421 g, 1.66 mmol) was added to a solution of tert-butyl 4-(5-phenyl-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate (0.63 g, 0.830 mmol) and KOH (0.140 g, 2.49 mmol) (crushed by mortar and pestle) in DMF (10 mL). The resulting mixture was heated to 60° C. for 3 hours. Ether (20 mL) and saturated Na2SO3 (10 mL) were added. The organic layer was separated, washed with brine, and dried over sodium sulfate. After removal of the solvent, the resulting residue was purified by chromatography (hexane:ethyl acetate, 3:1) to give tert-butyl 4-(3-iodo-5-phenyl-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate (0.40 g, 95%) as a solid. MS APCI (+) m/z 506.2 detected. 1H NMR (400 Hz, DMSO-d6) δ 8.30 (s, 1H), 7.60 (m, 3H), 7.49 (m, 2H), 3.63 (m, 4H), 2.95 (m, 4H), 1.51 (s, 9H).

Provenance & Evidence