Potassium Phosphate, Tribasic → [6-(4-{1-ethyl-1-[3-methyl-4-((E)-4,4,4-trifluoro-3-hydroxy-3-trifluoromethyl-1-butenyl)-phenyl]-propyl}-2-methyl-phenyl)-pyridin-3-yl]-acetic Acid Ethyl Ester

Participants

Reaction Conditions

Reaction Steps

Degassed N,N-dimethylformamide (0.15 mL) was added to (E)-4-(4-{1-ethyl-1-[3-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propyl}-2-methyl-phenyl)-1,1,1-trifluoro-2-trifluoromethyl-3-buten-2-ol (Example 26-(5); 14.0 mg, 0.0245 mmol), (2-bromo-pyridin-5-yl)acetic acid ethyl ester (Example 74-(1); 10.5 mg, 0.043 mmol), tetrakis(triphenylphosphine)palladium (0) (3.5 mg, 0.0030 mmol) and potassium phosphate (13.4 mg, 0.0631 mmol). After replacement with nitrogen, the mixture was heated while stirring at an external temperature of 85 to 95° C. for 10 hours. Water was added to the reaction mixture, followed by extraction with diethyl ether. The extract was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel chromatography (hexane/ethyl acetate=3/1) to give the title compound (12 mg, 80%).

Provenance & Evidence