Iodine → HCID 68774908, compound

Participants

Reaction Steps

At RT, a mixture of 5-(5-amino-2-chlorophenyl)-1-(2,6-difluorophenyl)-7-methyl-1H-pyrazolo[3,4-b]pyridin-6(7H)-one (230 mg, 0.59 mmol), iodine (151 mg, 0.59 mmol), copper(I) iodide (34 mg, 0.18 mmol) and cesium iodide (154 mg, 0.59 mmol) in DME (4.40 mL) was treated with isoamyl nitrite (0.48 mL, 3.57 mmol) drop wise over 3 min. The reaction mixture was stirred for 4 h, and filtered through a pad of celite washing with EtOAc (100 mL). The organic layer was washed sequentially with ˜2% NH4OH (20 mL), a solution of sodium thiosulfate (20 mL) and brine (20 mL), dried over MgSO4, filtered and concentrated. The crude residue was purified on the ISCO 12 g column (10-60% EtOAc in hexanes) affording the title compound as a white crystalline solid. MS (ESI, pos.ion) m/z: 497.9 (M+1).

Provenance & Evidence