Water → HCID 178497512, compound

Participants

Reaction Conditions

Reaction Steps

Bubble nitrogen through a mixture of trifluoro-methanesulfonic acid 3,5-dichloro-4-[(R)-2-oxo-cis-1-(4-triisopropylsilanyloxy-cyclohexyl)-pyrrolidin-3-ylmethyl]-phenyl ester (12.2 g, 18.87 mmol), 4-methoxycarbonylphenylboronic acid (4.1 g, 22.64 mmol), sodium carbonate (6 g, 56.6 mmol), 50 mL water, and 150 mL tetrahydrofuran for 30 min at room temperature. Add tetrakis(triphenylphosphine)palladium (1.7 g, 1.47 mmol) by weighing into a nitrogen filled vial and transferring the material as a dry solid to the reaction flask. Sparge an additional 5 min, then heat at 80° C. 1 hr. Dilute with 50 mL each of water and ethyl acetate, separate layers and extract the aqueous layer with 25 mL ethyl acetate. After combining the organic layers, wash with 50 mL brine, dry over magnesium sulfate and concentrate under vacuum. Purify on silica by eluting with 10-30% ethyl acetate in hexanes to give 11.1 g (93%) of product as an ivory foam: MS (m/z): 632 (M+).

Provenance & Evidence