Water → HCID 117759869, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl 3-cyclopropyl-3-(3-(((5-neopentyl-6-(((trifluoromethyl)sulfonyl)oxy)pyridin-3-yl)oxy)methyl)phenyl)propanoate (65.2 mg) in toluene (1.5 mL) were added (4-(trifluoromethoxy)phenyl)boronic acid (24.7 mg), 2M aqueous sodium carbonate solution (720 μL), and tetrakis(triphenylphosphine)palladium(0) (13.8 mg), and the mixture was heated in a microwave synthesizer (Anton Parr, Synthos3000) at 100° C. for 90 min. Water (1 mL) and ethyl acetate (3 mL) were added to the reaction solution and the mixture was stirred. The organic layer was passed through a phase separation filter, and the solvent was evaporated by an air blowing apparatus. The residue was purified by HPLC (column: YMC Triart C18, mobile phase: acetonitrile/10 mM aqueous ammonium hydrogen carbonate solution) and the solvent was evaporated by an air blowing apparatus. To the residue were added ethanol (1 mL) and 2M aqueous lithium hydroxide solution (180 μL), and the mixture was stirred at 60° C. for 1 hr. 1M Hydrochloric acid (360 μL) was added and the obtained solution was purified by HPLC (column: YMC Triart C18, mobile phase: acetonitrile/10 mM aqueous ammonium hydrogen carbonate solution), and the solvent was evaporated by an air blowing apparatus to give the title compound (14.9 mg).

Provenance & Evidence