Sodium Hydroxide → 1-(t-Butoxycarbonyl)-4-(6-phenyl-imidazo[1,2-a]pyridin-3-yl)-piperidine

Participants

Reaction Conditions

Reaction Steps

To a solution of 120 mg of 1-(t-butoxycarbonyl)-4-(6-bromo-imidazo[1,2-a]pyridin-3-yl)-piperidine and 78 mg of phenylboronic acid in 5 mL of toluene and 2.5 mL of ethanol was added 8 mg of tetrakis(triphenylphosphine)-palladium(0), followed by 0.85 mL of 1.25N sodium hydroxide solution. The reaction was stirred at 100° C. for 8 hours. The mixture was concentrated under reduced pressure and the mixture was partitioned between EtOAc and water. Aqueous layer was extracted with EtOAc (3×). The combined organic phase was washed with brine and dried over MgSO4. The residue was purified by flash chromatography with 50% EtOAc in hexanes followed by 100% EtOAc to give 141 mg of the title compound as a viscous oil, which was used in next step without further purification.

Provenance & Evidence