3-Bromo-6-chloroimidazo(1,2-b)pyridazine → (6-Chloroimidazo[1,2-b]pyridazin-3-yl)(5,7-difluoroquinolin-6-yl)methanol

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Reaction Steps

To a solution of 3-bromo-6-chloro-imidazo[1,2-b]pyridazine (2.40 g, 10.35 mmol) in 30 mL of THF was added EtMgBr (1 M in THF, 12.43 mL, 12.42 mmol) solution at rt. The solution was stirred for 30 min and a solution of 5,7-difluoroquinoline-6-carbaldehyde (2.0 g, 10.35 mmol) in 10 mL of THF was added. The resulting mixture was stirred at rt for additional 2 h and then quenched with 50 mL of NH4Cl solution. The solution was extracted with EtOAc and the combined organic layers were washed with water, brine, dried over Na2SO4 and concentrated in vacuo to afford 3.48 g (97%) of the title compound. LCMS (method B): [MH]+=347, tR=1.23 min.

Provenance & Evidence