Dichloromethane → 6-(2,6-Difluorophenyl)-2-methyl-3-nitropyridine

Participants

Reaction Conditions

Reaction Steps

A suspension of 2-bromo-6-methyl-5-nitropyridine (3 g, 13.82 mmol, Matrix Scientific), 2,6-difluorobenzeneboronic acid (4.37 g, 27.6 mmol, Alfa Aesar) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with DCM (0.564 g, 0.691 mmol, Strem) in Dioxane (60 mL) (degassed with argon for 30 min) and Na2CO3, 2.0 M (20.74 mL, 41.5 mmol) was heated to 100° C. under N2. After 3 h, 2,6-difluorobenzeneboronic acid (4.37 g, 27.6 mmol) was further added. After a total of 7 h, 2,6-difluorobenzeneboronic acid (2.18 g, 13.8 mmol) was further added. After a total of 9 h, the reaction mixture was cooled to 23° C., diluted with EtOAc (400 ml) and washed with brine (200 mL), dried over MgSO4, concentrated in vacuo and purified by silica gel chromatography (eluent: 5-10% EtOAc/hexane), affording 6-(2,6-difluorophenyl)-2-methyl-3-nitropyridine (1.931 g, 56%).

Provenance & Evidence