Hydrochloric Acid → 1-(3-(1-(7-Fluoroquinolin-6-yl)-1-hydroxyethyl)imidazo[1,2-b]pyridazin-6-yl)ethanone

Participants

Reaction Conditions

Reaction Steps

In a flask was charged with tetrakis-(triphenylphosphine)-palladium (51 mg, 0.044 mmol) under nitrogen. A solution of 1-(6-chloroimidazo[1,2-b]pyridazin-3-yl)-1-(7-fluoroquinolin-6-yl)ethanol (150 mg, 0.44 mmol) in DMF (10 mL) was added. The system was purged with nitrogen gas three times and tributyl-(1-ethoxy-vinyl)-stannane (0.16 ml, 0.46 mmol) was added. The temperature was increased to 100° C. and stirred overnight. The reaction mixture was cooled to room temperature, 3N HCl was added and the mixture was stirred for additional 4 hrs. Water was added and the mixture was then extracted with EtOAc, dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography (3% to 10% MeOH in CH2Cl2) to afford 70 mg (yield: 41%) title compound. LCMS (method B): [MH]+=351, tR=2.01 min.

Provenance & Evidence