Sodium Carbonate → tert-Butyl 4-(6-(tert-butoxycarbonylamino)-5-(5-phenyl-1,3,4-oxadiazol-2-yl)pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate

Participants

Reaction Conditions

Reaction Steps

A mixture of tert-butyl N-[5-bromo-3-(5-phenyl-1,3,4-oxadiazol-2-yl)-2-pyridyl]-N-tert-butoxycarbonyl-carbamate (300 mg, 0.5799 mmol), tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylate (215.2 mg, 0.6959 mmol), dichloropalladium; triethylphosphane (12.00 mg, 0.02900 mmol) and Na2CO3 (184.4 mg, 1.740 mmol) in DMF (3.000 mL) was heated to 60° C. for 16 hours. Analysis indicated that there was starting material remaining so the reaction was heated to 140° C. in the microwave for a further 2 hours. The reaction mixture was allowed to cool to ambient temperature, diluted with DCM and water and the two layers separated. The organics were washed with 1M NaOH solution, dried (Na2SO4), filtered and concentrated in vacuo. The resultant residue was purified by column chromatography (EtOAc/Petroleum ether) to give the desired product that was used directly in the next step without further purification (142 mg, 47% Yield). MS (ES+) 302.31.

Provenance & Evidence