Tetrahydrofuran → 4-(4-Acetamidophenyl)pyridine

Participants

Reaction Steps

A round bottom flask was charged with a 2 N Na2CO3 solution (4 equivalents) and THF and the mixture was sparged with N2 through a dispersion tube. 4-Bromopyridine hydrochloride (1 equivalent) and N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]acetamide (1.2 equivalents) were subsequently added, followed by Pd(dppf)2Cl2 (2.5 mol %). The reaction mixture was refluxed overnight, cooled to room temperature and diluted with EtOAc. The two phases were separated and the organic phase was washed with a 2 N Na2CO3 solution, brine, and dried (Na2SO4). Evaporation of the solvent under reduced pressure and purification by silica gel chromatography afforded the desired product as a white solid. MH+=213.1.

Provenance & Evidence