Tert-butyl 4-(trifluoromethanesulfonyloxy)-1,2,3,6-tetrahydropyridine-1-carboxylate → tert-Butyl 4-[(2-methylpyrimidin-5-yl)ethynyl]-3,6-dihydropyridine-1(2H)-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of CuCl (1 mg, 0.01 mmol) and PdCl2(PPh3)2 (0.003 g, 0.004 mmol) in DMF (2 mL) were added 2-methyl-5-[(trimethylsilyl)ethynyl]pyrimidine (0.088 g, 0.462 mmol) and tert-butyl 4-{[(trifluoromethyl)sulfonyl]oxy}-3,6-dihydropyridine-1(2H)-carboxylate (Example 2e) (0.183 g, 0.555 mmol) at room temperature. The reaction mixture was stirred for 8 h at 80° C. After cooling, the mixture was quenched with 1N HCl and extracted with ether (3×). The combined organic layers were washed with saturated aqueous NaHCO3 solution, brine and dried. Filtration and evaporation afforded a brown oil, which was purified on HPLC to give the subtitle compound (0.062 g, 45%).

Provenance & Evidence