Sodium Carbonate → 7-Ethyl-4-(4'-(ethylsulfonyl)-2'-fluoro-6-methoxy-[1,1'-biphenyl]-3-yl)-7H-imidazo[4,5-c]pyridazine

Participants

Reaction Conditions

Reaction Steps

To 2-(4′-(ethylsulfonyl)-2′-fluoro-6-methoxy-[1,1′-biphenyl]-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (Preparation 69, 90 mg, 0.21 mmol) in dioxane (2.5 mL) and water (1 mL) was added 4-chloro-7-ethyl-7H-imidazo[4,5-c]pyridazine (Preparation 8, 40 mg, 0.21 mmol) and sodium carbonate (68 mg, 0.64 mmol). The reaction was degassed and tetrakis(triphenylphosphine) palladium(0) (25 mg, 0.02 mmol) was added. The reaction was further degassed and then heated to 110° C. for 2 hours and then cooled to room temperature. The reaction mixture was diluted with EtOAc (40 mL) was passed through celite and the solvent removed in vacuo. The crude material was purified by reverse phase column chromatography eluting with a gradient of 0.1% formic acid in MeCN/water. The resulting residue was dissolved in DMSO (1 mL) and purified using preparative HPLC to give the title compound as a colourless solid in 26% yield, 24 mg.

Provenance & Evidence