Cesium fluoride → HCID 136200885, compound

Participants

Reaction Conditions

Reaction Steps

2-Chloro-5-iodo-3′-(trifluoromethyl)biphenyl-4-ol (Preparation 51, 230 mg, 0.57 mmol) was dissolved in acetonitrile (3 mL), 4-(tributylstannyl)pyridazine (273 mg, 0.75 mmol), caesium fluoride (173 mg, 1.14 mmol), copper iodide (22 mg, 0.114 mmol) and tetrakis(triphenylphosphine)palladium (0) (70 mg, 0.06 mmol) were added. The reaction was stirred at 45° C. for 1.5 hours and then after cooling to room temperature was partitioned between ethyl acetate (100 mL) and water (50 mL) containing 0.880 ammonia (1 mL). The mixture was stirred for 20 minutes. The ethyl acetate phase was separated and washed with an aqueous solution of potassium fluoride (1.5 g in 20 mL), 1M hydrochloric acid (20 mL) and aqueous ammonia (1 mL 0.880 in 50 mL water). The ethyl acetate was dried over MgSO4, filtered and evaporated. The residue was chromatographed on silica eluting with a gradient of dichloromethane:methanol 100:0 to 95:5 to give the title compound (144 mg, 0.40 mmol, 71%) as a white solid.

Provenance & Evidence