Potassium Carbonate → (4'-{4-[(R)-1-(2-Fluoro-phenyl)-ethoxycarbonylamino]-5-methyl-isoxazol-3-yl}-biphenyl-4-yl)-acetic acid

Participants

Reaction Conditions

Reaction Steps

[3-(4-Bromo-phenyl)-5-methyl-isoxazol-4-yl]-carbamic acid (R)-1-(2-fluoro-phenyl)-ethyl ester (0.080 g, 0.16 mmol), (4-ethoxycarbonylmethylphenyl)boronic acid, pinacol ester (0.055 g, 0.19 mmol), potassium carbonate (0.055 g, 0.40 mmol), and bis(triphenylphosphine)palladium(II) dichloride (0.011 g, 0.016 mmol) were combined in 2:1 DME:H2O and degassed with N2 for 5 minutes. The reaction was stirred at 90° C. for 3 hours, until no starting material was seen by analytical LCMS. 1N Aqueous LiOH (0.5 mL) was added, and the reaction was stirred at room temperature until no ester starting material was seen by analytical LCMS. After acidic work-up, the crude material was purified by preparative HPLC to give the title compound. Mass spectometric data [M+H]=475.

Provenance & Evidence