Sodium Carbonate → (R)-3',5'-Dichloro-3-fluoro-4'-[2-oxo-1-(4-triisopropylsilanyloxy-piperidin-1-yl)-pyrrolidin-3-ylmethyl]-biphenyl-4-carbonitrile

Participants

Reaction Steps

Purge with nitrogen for 10 minutes a mixture of (R)-trifluoro-methanesulfonic acid 3,5-dichloro-4-[2-oxo-1-(4-triisopropylsilanyloxy-piperidin-1-yl)-pyrrolidin-3-ylmethyl]-phenyl ester (0.18 g, 0.28 mmol), 3-fluoro-4-cyanophenylboronic acid (0.055 g, 0.33 mmol), sodium carbonate (0.089 g, 0.84 mmol) in THF (10 mL) and water (3 mL). Add Pd(PPh3)4 (0.016 g, 0.01 mmol) to the mixture. Stir the reaction at 80° C. for 1 hour. Cool the reaction, dilute with ethyl acetate, and wash with water and brine. Dry the organic layer (Na2SO4), remove the solvent in vacuo to afford crude product, and purify on silica gel column with 0% to 50% ethyl acetate in hexanes gradient to afford 0.151 g of the titled product. MS (m/z): 617 (M+).

Provenance & Evidence