Sodium Carbonate → 3-(2-Chloro-4-pyridin-3-yl-benzyl)-1-cyclohex-3-enyl-pyrrolidin-2-one

Participants

Reaction Steps

Combine 3-(4-bromo-2-chloro-benzyl)-1-cyclohex-3-enyl-pyrrolidin-2-one (370 mg, 1.01 mmol), 3-pyridine boronic acid (372 mg, 3.03 mmol), tetrakis(triphenylphosphine)palladium(0) (116 mg, 0.10 mmol), Na2CO3 (2.14 g, 20.2 mmols), water (1.5 mL), 1,2-dimethoxy-ethane (8 mL) and heat at 80° C. for 20 hours. Cool the reaction mixture to room temperature, add saturated aqueous NaHCO3 (5 mL) and extract with EtOAc (3×10 mL). Dry the organic layer over anhydrous Na2SO4, remove the solvent and purify the residue by chromatography over silica gel eluting with EtOAc in hexane (0 to 100%) to obtain 3-(2-chloro-4-pyridin-3-yl-benzyl)-1-cyclohex-3-enyl-pyrrolidin-2-one as a clear oil (60 mg, 16%): MS (ES+) m/z=367 (M+H)+.

Provenance & Evidence