Tributylvinyltin → 1-(t-Butoxycarbonyl)-4-(6-vinyl-imidazo[1,2-a]pyridin-3-yl)-piperidine

Participants

Reaction Steps

To a solution of 95 mg of 1-(t-butoxycarbonyl)-4-(6-bromo-imidazo[1,2-a]pyridin-3-yl)-piperidine (from Example 274, Step A), and 158 mg of tributyl(vinyl)tin in 6 mL toluene was added 5.3 mg of dichlorobis (triphenyl phosphine)-palladium(II). The mixture was refluxed for 2 hours. The reaction was cooled down to r.t. and partitioned between CH2Cl2and water. Aqueous layer was extracted with CH2Cl2 (3×). The combined organic phase was washed with brine and dried over MgSO4. After concentration, the residue was purified by prep TLC (100% EtOAc) to give 90 mg of the title compound as a viscous oil, which was used in next step without further purification.

Provenance & Evidence