Potassium Phosphate, Tribasic → [4'-(1-{4-[3-(t-butyl-dimethyl-silanyloxy)-4,4-dimethyl-pentyl]-3-methyl-phenyl}-1-ethyl-propyl)-3-fluoro-2'-methyl-biphenyl-4-yl]-acetic Acid Methyl Ester

Participants

Reaction Conditions

Reaction Steps

Degassed toluene (0.12 mL) and water (0.012 mL) were added to t-butyl-(1-{2-[4-(1-ethyl-1-{4-[4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl]-3-methyl-phenyl}-propyl)-2-methyl-phenyl]-ethyl}-2,2-dimethyl-propoxy)dimethylsilane (Example 23-(1); 16.5 mg, 0.0272 mmol), palladium (II) acetate (0.9 mg, 0.004 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxy-1,1′-biphenyl (3.3 mg, 0.0080 mmol) and potassium phosphate (19.0 mg, 0.0895 mmol). After replacement with nitrogen, (4-chloro-2-fluoro-phenyl)acetic acid methyl ester (Example 40; 7.4 mg, 0.037 mmol) was added. After replacement with nitrogen, the mixture was heated while stirring at an external temperature of 96 to 104° C. for one hour. The reaction mixture was diluted with diethyl ether and filtered through cotton plug, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography (hexane/ethyl acetate=50/1) to give the title compound (13.5 mg, 77%).

Provenance & Evidence