N-Iodosuccinimide → 2-Fluoro-6-iodopyridin-3-amine

Participants

Reaction Steps

To a solution of 2-fluoropyridin-3-amine (5.00 g, 44.60 mmol) in DMF (100 mL) was added N-iodosuccinimide (11.04 g, 49.06 mmol). The resulting mixture was stirred overnight. The reaction mixture was partitioned between EtOAc and water. The organic layer was dried with MgSO4 and concentrated. The residue was purified on silica eluted 0 to 50% EtOAc in Heptane. 2-fluoro-6-iodopyridin-3-amine was obtained as a dark tan solid (8.8674 g, 83%). To an ice cooled mixture of tert-Butyl nitrite (356.8 uL, 3.000 mmol) and Copper(II) bromide (536.0 mg, 2.400 mmol) in Acetonitrile (5 mL) was added 2-fluoro-6-iodopyridin-3-amine was obtained as a dark tan solid (476.0 mg, 2.000 mmol). The resulting mixture was stirred overnight allowing warming to room temperature. The mixture was filtered through Celite. The filtrated was concentrated. The residue was partitioned between Et2O and saturated NH4Cl. The organic layer was dried with MgSO4, and then concentrated. The residue was purified on silica eluted with 0 to 20% EtOAc in Heptane. 3-Bromo-2-fluoro-6-iodopyridine was obtained as a yellow solid (407.1 mg, 57%)

Provenance & Evidence