N-Iodosuccinimide → N-(6-(6-chloro-5-(3-(difluoromethoxy)phenylsulfonamido)pyridin-3-yl)-3-iodoimidazo[1,2-b]pyridazin-2-yl)acetamide

Participants

Reaction Steps

To a CH2Cl2 (20 mL) solution N-(6-(6-chloro-5-(3-(difluoromethoxy)phenylsulfonamido)pyridin-3-yl)imidazo[1,2-b]pyridazin-2-yl)acetamide (315.0 mg, 619.0 μmol) was added n-iodosuccinimide (195.0 mg, 866.6 μmol, Alfa Aesar, Ward Hill, Mass.) as a solid in a single portion. The solution turned dark brown and was maintained at rt for 1 h. The solution was concentrated for purification by MPLC (CombiFlash® Companion®, Teledyne Isco, Lincoln, Nebr.). The crude residue was taken up in minimal CH2Cl2/MeOH and absorbed onto a 25 g silica loading cartridge and passed through a Redi-Sep® pre-packed silica gel column (Teledyne Isco, Lincoln, Nebr.) (80 g) using a gradient of 1% MeOH in CH2Cl2 to 10% MeOH in CH2Cl2 to afford N-(6-(6-chloro-5-(3-(difluoromethoxy)phenylsulfonamido)pyridin-3-yl)-3-iodoimidazo[1,2-b]pyridazin-2-yl)acetamide (370.0 mg, 94.16% yield) as a brown solid. LCMS (ESI positive ionization) m/z: 635 (M+1).

Provenance & Evidence