Cesium fluoride → Methyl 2-fluoro-6-(pyrimidin-2-yl)benzoate

Participants

Reaction Conditions

Reaction Steps

Methyl 2-fluoro-6-iodobenzoate (17 g, 61 mmol, 1 eq.) and 2-(tributylstannyl)pyrimidine (26.7 g, 72 mmol, 1.2 eq.) were dissolved in 120 ml of dry DMF under nitrogen atmosphere. Cesium fluoride (18.1 g, 119 mmol, 2 eq., highly hygroscopic) was added and nitrogen was bubbled into the suspension for 5 minutes. While bubbling, Copper iodide (1.1 g, 5.77 mmol 0.1 eq.) and tetrakis(triphenylphosphine)palladium(0) (6.9 g, 5.97 mmol, 0.1 eq) were added. The mixture was then heated at 115° C. for 45 minutes. After that, it was allowed to cool to room temperature, diluted with a large volume of AcOEt and filtered over celite. The resulting liquid phase was washed thoroughly with a saturated aqueous solution of ammonium chloride to remove DMF, dried with sodium sulphate, filtered and evaporated to dryness.

Provenance & Evidence