Imidazo[1,2-a]pyridine-6-carbaldehyde → (Rac)-(6-chloro-imidazo[1,2-b]pyridazin-3-yl)-imidazo[1,2-a]pyridin-6-yl-methanol

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Reaction Steps

Ethyl magnesium bromide (3 M in Et2O, 333 μL, 1 mmol) was added to a solution of 3-bromo-6-chloro-imidazo[1,2-b]pyridazine (116 mg, 0.5 mmol) in THF (5 mL) at rt . The RM was stirred for 30 min and imidazo[1,2-a]pyridine-6-carbaldehyde (154 mg, 2 mmol) in THF (3 mL) was added dropwise. After 1 h the RM was extracted with a solution of NH4Cl and EtOAc. The combined organic phases were dried over Na2SO4, concentrated under reduced pressure, and purified by flash chromatography (CombiFlash® Companion System®, with RediSep® silica gel column, Hexane/EtOAc=95:5->0:100) to afford the title compound as a yellowish crystalline compound (tR 2.72 min (conditions 3), MH+=300.2).

Provenance & Evidence