Potassium Phosphate, Tribasic → 3-Pyridinecarboxylic acid,4-(trifluoromethyl)-6-[4-(trifluoromethyl)phenyl]-,methyl ester

Participants

Reaction Conditions

Reaction Steps

To a solution of bis(triphenylphosphine)palladium(II)chloride (0.84 g, 1.2 mmol), methyl 6-chloro-4-(trifluoromethyl)nicotinate (9.58 g, 40 mmol) and 4-(trifluoromethyl) benzene boronic acid (10.1 g, 52 mmol) in degassed toluene (200 ml) was added aqueous 2 M K3PO4 (40 ml). The suspension was stirred at 80° C. for 16 h. The reaction mixture was cooled to RT, ice water was added and the mixture was extracted three times with diethyl ether. The organic phases were washed with aqueous 10% NaCl, dried (Na2SO4) and evaporated. Purification by flash-chromatography on silica gel (dichloromethane/heptane 2:1 to 1:1) gave 9.91 g (28.3 mmol, 71%) of the title compound as off-white powder.

Provenance & Evidence