Potassium Carbonate → 1,1-dimethylethyl (3S)-3-({4-[3-fluoro-3'-(methyloxy)-4-biphenylyl]-5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl}methyl)-1-pyrrolidinecarboxylate

Participants

Reaction Conditions

Reaction Steps

A solution of 1,1-dimethylethyl (3S)-3-{[4-(4-bromo-2-fluorophenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl]methyl}-1-pyrrolidinecarboxylate (0.499 mmol) in dioxane (3 mL) was treated with 3-methoxyphenylboronic acid pinacol ester (0.513 mmol), dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II)-dichloromethane adduct (30 mg), and 2M aq potassium carbonate (1.5 mL). The reaction mixture was purged with nitrogen, sealed, and stirred at 110° C. for 2 h. The solution was cooled to room temperature and the dioxane layer separated from the aqueous layer. The dioxane layer was removed via pipette and was passed through a plug of celite and sodium sulfate. The plug was washed with dioxane (10 mL). All dioxane filtrates were combined and concentrated in vacuo. Silica gel chromatography (100% ethyl acetate) was utilized in purifying the title compound (212 mg, 88%). MS(ES)+ m/e 469.3 [M+H]+.

Provenance & Evidence