Hydrochloric Acid → 2-Chloro-6-propylimidazo[1,2-b]pyridazine

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Under a nitrogen stream, a solution of n-propylzinc bromide in tetrahydrofuran (0.5 M, 7.98 ml, 3.99 mmol) was diluted with toluene (5.0 ml), and 2,6-dichloroimidazo[1,2-b]pyridazine (0.50 g, 2.66 mmol) and bis(triphenylphosphine)palladium(II) dichloride (0.19 g, 0.27 mmol) were added thereto, and the reaction mixture was stirred for 2 hours at 80° C. After cooling, to the reaction mixture was added cold water (50 ml), acidified with dilute hydrochloric acid, extracted with ethyl acetate, and the extracts were washed with dilute hydrochloric acid, a saturated saline, an aqueous saturated sodium bicarbonate solution and a saturated saline in this order. The resulting organic layer was dried over anhydrous magnesium sulfate, filtrated and concentrated. The concentrated residue was purified by silica gel column chromatography (ethyl acetate:hexane=3:7) to give the title compound as white crystals. The yield was 0.31 g (59.6%).

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