Cesium fluoride → Ethyl 2-pyridazin-4-yl-4-(trifluoromethyl)benzoate

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To a solution of 2-iodo-4-trifluoromethylbenzoic acid ethyl ester (200 mg, 0.581 mmol) in acetonitrile (5 mL) was added 4-(tributylstannyl)pyridazine (214 mg, 0.581 mmol) and caesium fluoride (176 mg, 1.16 mmol). The solution was sparged with nitrogen before the addition of tetrakis(triphenylphosphine)palladium (0) (26 mg, 0.023 mmol) and copper iodide (22 mg, 0.116 mmol). The reaction mixture was sparged with nitrogen then heated at 45° C. for 2 hours. The reaction mixture was cooled to ambient temperature, diluted with ethyl acetate and filtered through Celite™. An aqueous solution of potassium fluoride was added and the reaction mixture was stirred for 16 hours. The organic layer was separated, washed with water, followed by a saturated aqueous solution of sodium chloride. The organic layer was dried over anhydrous sodium sulphate, filtered and concentrated in vacuo. The material was purified by column chromatography (100-200 silica, eluting with 60% ethyl acetate in heptane). Fractions containing product were combined and concentrated in vacuo to obtain the title compound as a solid (140 mg).

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