Potassium Phosphate, Tribasic → (4'-{1-Ethyl-1-[4-(3-ethyl-3-hydroxy-pentyl)-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 (3.1 mg, 0.0139 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (11.4 mg, 0.0279 mmol) and potassium phosphate (59.3 mg, 0.0279 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; 30.3 mg, 0.14 mmol) and 3-ethyl-1-(4-{1-ethyl-1-[3-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propyl}-2-methyl-phenyl)-pentan-3-ol (Example 29; 49.2 mg, 0.0998 mmol) in toluene (0.250 mL) was added, and the mixture was stirred in a nitrogen atmosphere at 100° C. for three hours. After filtration through cotton plug, the filtrate was concentrated under reduced pressure. The residue was purified by thin layer silica gel chromatography (15% ethyl acetate/hexane) to give the title compound (37.5 mg, 70%).

Provenance & Evidence