Cesium fluoride → Tert-butyl(4-(2,4-dimethyl-1,3-thiazol-5-yl)-2-{[3-(propylsulfonyl)phenyl]ethynyl}phenoxy)acetate

Participants

Reaction Steps

A solution of tert-butyl(4-bromo-2-{[3-(propylsulfonyl)phenyl]ethynyl}phenoxy)acetate (Intermediate 191; 100 mg; 0.20 mmol), 2,4-dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-thiazole (73 mg; 0.30 mmol) was placed in a microwave vial and treated with caesium fluoride (93 mg; 0.61 mmol) and bis(triphenylphosphine)palladium(II) chloride (14 mg; 0.02 mmol). The tube was sealed and degased with N2 before adding dioxane (2 ml) and water (1 ml). The resulting reaction mixture was irradiated in a microwave reactor at 120° C. for 10 minutes. The reaction mixture was taken up in EtOAc and washed with water and brine. The organic phase was dried over MgSO4, filtered, concentrated and purified by flash column chromatography (silica), eluting with cyclohexane containing increasing amounts of EtOAc affording the title compound as a brown sticky solid (78 mg, 73%).

Provenance & Evidence