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

Participants

Reaction Steps

3-Bromo-6-chloro-imidazo[1,2-b]pyridazine (4.40 g, 18.95 mmol) was dissolved THF (189 mL) and under nitrogen conditions, ethylmagnesium bromide solution (3 M, 6.32 mL) was added slowly. The RM was stirred at rt for 15 min then a solution of 5,7-difluoro-quinoline-6-carbaldehyde (Intermediate F, 3.66 g, 18.95 mmol) in THF was added. It was stirred at rt for 30 min. The reaction was quenched with 10% NH4Cl. The precipitate was filtered off and a first part of the title compound was obtained as a white solid. The filtrate was concentrated and was taken up with 10% NH4Cl. The precipitate was filtered off and was washed with EtOAc. A second part of the title compound was obtained as a brown solid (tR 0.8 min (conditions 2), MH+=347).

Provenance & Evidence