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

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).

1. customwas degassed with nitrogen
2. temperaturerefluxed overnight
3. concentrationThe reaction mixture was concentrated
4. extractionextracted with ethyl acetate
5. dry with materialThe ethyl acetate layer was dried on Na2SO4
6. customfurther purified by column chromatography

ORD record

ord-d77d659e1a7f4c788f1072122242618b

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08946697B1