Sodium Carbonate → HCID 69159599, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-chloropyridazin-3(2H)-one (1.91 g, 14.6 mmol), bis(pinacolato)diboron (3.89 g, 15.3 mmol), potassium acetate (2.14 g, 21.8 mmol), dioxane (100 ml) and [1,1′-bis(diphenylphosphino)ferrocene]-dichloropalladium (0.4 g) was degassed (N2), then heated at 90° C. for 16 hours under nitrogen. More catalyst (0.45 g) was added and the mixture heated 7 hours more. After cooling to room temperature 4-bromo-3-fluorobenzotrifluoride (4.5 g, 18.5 mmol) was added along with 2M aqueous sodium carbonate solution (35 ml) and a further portion of catalyst (450 mg). The mixture was heated to 115° C. for 24 h, then cooled to room temperature, diluted with ethyl acetate (250 ml) and filtered. The layers were separated, the aqueous phase extracted with ethyl acetate (100 ml) and the combined organic layers evaporated. The residue was purified by flash column chromatography eluting with 5% methanol in dichloromethane to give the title compound (795 mg, 21%).

Provenance & Evidence