Cesium fluoride → Methyl 6-(4-(trifluoromethyl)phenyl)nicotinate

Participants

Reaction Conditions

Reaction Steps

To an ambient temperature solution of 6-chloro-nicotinic acid methyl ester (12.4 g, 72 mmol) and 4-(trifluoromethyl)phenylboronic acid (15 g, 79 mmol) in dioxane (270 mL) is added CsF (38.3 g, 252 mmol) and the reaction mixture is degassed with nitrogen. PdCl2(dppf) (1.5 g) is added and the reaction mixture is heated to 100° C. over weekend. The reaction mixture was diluted with ethyl acetate, filtered through celite. The filtrate is concentrated. Purification of the crude product by column on silica gel (hexanes/ethyl acetate) gives 6-(4-trifluoromethyl-phenyl)-nicotinic acid methyl ester (18.3 g, 82.3% yield).

Provenance & Evidence