Potassium Carbonate → 3',5'-dichloro-4'-[(R)-2-oxo-1-(tetrahydro-pyran-4-yl)-pyrrolidin-3-ylmethyl]-biphenyl-4-carboxylic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

Treat a solution of trifluoro-methanesulfonic acid 3,5-dichloro-4-[(R)-2-oxo-1-(tetrahydro-pyran-4-yl)-pyrrolidin-3-ylmethyl]-phenyl ester (3.0 g, 6.3 mmol), 4-methoxycarbonylphenylboronic acid (2.3 g, 13 mmol), and tetrakis(triphenylphosphine)palladium(0) (0.73 g, 0.63 mmol) in dimethoxyethane (40 mL) with 2M aqueous potassium carbonate (9.5 mL). Heat the mixture to 80° C. overnight. Cool to room temperature, quench with 1N hydrochloric acid and extract with ethyl acetate. Wash the organic layer with brine, dry over magnesium sulfate, and filter. Purify the crude material by silica gel chromatography using hexanes:ethyl acetate to afford 2.56 g (88%) of desired product: MS (m/z): 462 (M+).

Provenance & Evidence