3-Bromo-6-chloroimidazo(1,2-b)pyridazine → (Rac)-(6-chloro-imidazo[1,2-b]pyridazin-3-yl)-(3-methyl-3h-benzoimidazol-5-yl)-methanol

Participants

Reaction Steps

3-Bromo-6-chloro-imidazo[1,2-b]pyridazine (850 mg, 3.47 mmol) was dissolved in THF (50 mL) under Argon. Ethylmagnesium bromide solution (1 M, 3.47 mL) was added and the mixture was stirred at rt for 20 min. Then 3-methyl-3H-benzoimidazole-5-carbaldehyde in THF (10 mL) was slowly added and the mixture was stirred at rt for 18 h. The mixture was quenched with water and NaHCO3. It was extracted with EtOAc twice and some MeOH to dissolve the solids. The combined organic layers were washed with brine, dried over Na2SO4, filtered and evaporated. The residue was purified by flash chromatography (CombiFlash® Companion System®, with 40 g RediSep® silica gel column, DCM/MeOH=100:0->94:6 in 25 min then up to 11% MeOH). The collected fractions containing product were evaporated and the residue was dried under vacuum to afford the title compound as a pink foam (tR 1.79 min (conditions 8), MH+=314).

Provenance & Evidence