Cesium carbonate → 2-[4-[(1-Methylethyl)oxy]-3-(trifluoromethyl)phenyl]-1,3-thiazole

Participants

Reaction Conditions

Reaction Steps

To a solution of 4,4,5,5-tetramethyl-2-[4-[(1-methylethyl)oxy]-3-(trifluoromethyl)phenyl]-1,3,2-dioxaborolane (D42) (160 mg), 2-bromo-1,3-thiazole (119 mg) and cesium carbonate (237 mg) in acetonitrile (15 mL) and water (3.75 mL) stirred under nitrogen at room temperature was added PdCl2(dppf)-CH2Cl2 adduct (39.6 mg) in one charge. The reaction vessel was sealed and heated under microwave at 120° C. for 1 h. After cooling the reaction, the reaction mixture was filtered and the filtrate was partitioned between ethyl acetate (150 mL) and saturated brine (50 mL). The organic phase was dried over sodium sulphate and evaporated in vacuo. The crude product was purified by column chromatography to give 2-[4-[(1-methylethyl)oxy]-3-(trifluoromethyl)phenyl]-1,3-thiazole (D66) (73 mg). MS (ES): C13H12F3NOS requires 287. found 288.1 (M+H+).

Provenance & Evidence