Potassium Phosphate, Tribasic → 2-Methyl-8-(4-p-tolylpyridin-2-yl)benzofuro[2,3-b]pyridine

Participants

Reaction Steps

A mixture of 2-methyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzofuro[2,3-b]pyridine (2.5 g, 8.03 mmol), 2-chloro-4-(p-tolyl)pyridine (1.80 g, 8.83 mmol), Pd2(dba)3 (0.147 g 0.161 mmol), dicyclohexyl(2′,6′-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine (0.264 g, 0.642 mmol), potassium phosphate (5.96 g, 28.1 mmol), toluene (100 mL) and water (10 mL) was degassed with nitrogen and then refluxed overnight. The reaction mixture was concentrated and extracted with ethyl acetate. The ethyl acetate layer was dried on Na2SO4 and then further purified by column chromatography using ethyl acetate in hexanes to give 2-methyl-8-(4-(p-tolyl)pyridin-2-yl)benzofuro[2,3-b]pyridine (2.0 g, 5.71 mmol, 71% yield).

Provenance & Evidence