Cesium carbonate → HCID 71087321, compound

Participants

Reaction Conditions

Reaction Steps

To a microwave vial were added 4-(4-bromo-2-chloro-6-fluorophenyl)-5-{[(3S)-1-(cyclopropylcarbonyl)-3-pyrrolidinyl]methyl}-2,4-dihydro-3H-1,2,4-triazol-3-one (0.027 mmol), 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-benzofuran (0.04 mmol), cesium carbonate (0.08 mmol), and dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II)-dichloromethane adduct (0.0012 mmol). The mixture was purged with nitrogen and suspended in 1,4-dioxane (0.3 mL) and water (0.15 mL). The mixture was heated for 15 h at 100° C. Analysis by LCMS indicated desired product formation and consumption of starting material. The mixture was filtered through a syringe filter and purified by reverse phase HPLC (10-90% acetonitrile/water+0.1% TFA). The desired fractions were collected and added to a separatory funnel containing ethyl acetate. The aqueous phase was adjusted to pH˜6 with 1N aq HCl. The aqueous phase was extracted with ethyl acetate (3×), and the combined organics were washed with brine, dried over Na2SO4, and concentrated to afford the title product as an off-white solid and nearly equal mixture of atropisomeric diastereomers (7.0 mg, 54%). MS(ES)+ m/e 481.0 [M+H]+.

Provenance & Evidence