Potassium Phosphate, Tribasic → (4'-{1-Ethyl-1-[4-(2-hydroxy-3,3-dimethyl-butoxy)-3-methyl-phenyl]-propyl}-3-fluoro-2'-methyl-biphenyl-4-yl)acetic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

A solution of palladium acetate (3.8 mg, 0.0169 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (13.9 mg, 0.0339 mmol) and potassium phosphate (72.0 mg, 0.33 mmol) in water (0.050 mL) and toluene (0.200 mL) was stirred for three minutes. A solution of (4-chloro-2-fluoro-phenyl)acetic acid methyl ester (Example 40; 36.8 mg, 0.18 mmol) and 1-(4-{1-ethyl-1-[3-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propyl}-2-methyl-phenoxy)-3,3-dimethyl-butan-2-ol (Example 31; 60.0 mg, 0.12 mmol) in toluene (0.3 mL) was added, and the mixture was stirred in a nitrogen atmosphere at 100° C. for one hour. After filtration through cotton plug, the filtrate was concentrated under reduced pressure. The residue was purified by thin layer silica gel chromatography (8% ethyl acetate/hexane) to give the title compound (21.1 mg, 32%).

Provenance & Evidence