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

Participants

Reaction Conditions

Reaction Steps

A solution of (3S)-3-{[4-(4-bromo-2-fluorophenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl]methyl}-N,N-dimethyl-1-pyrrolidinecarboxamide (0.146 mmol) in dioxane (2 mL) was treated with 4-methoxyphenylboronic acid (0.165 mmol), dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II)-dichloromethane adduct (10 mg), and 2M aq potassium carbonate (1 mL). The reaction mixture was purged with nitrogen, sealed, and stirred at 110° C. for 2 h. The solution was cooled to room temperature. The dioxane layer separated from the aqueous layer and was removed via pipette and passed through a plug of celite and sodium sulfate. The plug was washed with dioxane (4 mL). All dioxane filtrates were combined and concentrated in vacuo. Reverse phase HPLC (10-70% acetonitrile/water+0.1% NH4OH) was utilized in purifying the title compound (26 mg, 39%). MS(ES)+ m/e 440.0 [M+H]+.

Provenance & Evidence