Sodium Carbonate → HCID 178455346, compound

Participants

Reaction Steps

Combine trans-3-(4 bromo-2-chloro-benzyl)-1-[4-(tert-butyl-dimethyl-silanyloxy)-cyclohexyl]-piperidin-2-one (Preparation 65) (0.2 g, 0.49 mmol), 3-pyridine boronic acid (0.2 g, 1.49 mmol), tetrakis(triphenylphosphine)palladium(0) (0.06 g, 0.05 mmol), Na2CO3 (1.1 g, 9.95 mmols), water (1.5 mL), 1,2-dimethoxy-ethane (7 mL) and heat at 80° C. for 24 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 50 to 100% EtOAc in hexane) to obtain trans-1-[4-(tert-butyl-dimethyl-silanyloxy)-cyclohexyl]-3-(2-chloro-4-pyridine-3-yl-benzyl)-piperidin-2-one as a white solid (0.2 g, 80%).

Provenance & Evidence