Water → [1-(5-Acetyl-pyridin-2-yl)-cyclopropyl]-carbamic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

To a solution of [1-(5-Iodo-pyridin-2-yl)-cyclopropyl]-carbamic acid tert-butyl ester (100 mg, 0.278 mmol) in anhydrous DMF (1 mL) was added tributyl-(1-ethoxy-vinyl)-stannane (0.103 mL, 0.305 mmol) followed by tetrakis(triphenylphosphane)palladium (0) (32.1 mg, 0.028 mmol). The mixture was stirred at 100° C. under an atmosphere of argon. After 16 h, pyridinium p-toluenesulfonate (77.0 mg, 0.306 mmol) was added along with 0.5 mL of water and the mixture was stirred at rt for 1 h. The reaction was diluted with 10 mL of 10% citric acid and was extracted with EtOAc (3×30 mL). The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. The product was purified by column chromatography (10 g biotage SNAP column, 5-40% EtOAc in hexanes) to give the title compound as a yellow solid (74.7 mg, 97%).

Provenance & Evidence