Cesium fluoride → Methyl 3-(5-methylpyridin-2-yl)-5-(1,3-oxazol-2-yl)benzoate

Participants

Reaction Conditions

Reaction Steps

To a degassed solution of methyl 3-bromo-5-(5-methylpyridin-2-yl)benzoate (1.0 g, 3.27 mmol) in 1,4-dioxane (20 mL) was added cesium fluoride (1.49 g, 9.80 mmol), 2-(tributylstannyl)-1,3-oxazole (2.34 g, 6.53 mmol) and Bis(tri-t-butylphosphine) palladium (83 mg, 0.163 mmol). The mixture was heated to 90° C. under nitrogen for 16 h, after which the reaction was cooled to 20° C. Ethyl acetate (200 mL) and saturated sodium bicarbonate solution (200 mL) were added. The organic layer was isolated and the aqueous layer was extracted with ethyl acetate (2×). The combined organic extracts were washed with brine, dried over sodium sulfate, filtered and concentrated. The residue was run through silica gel chromatography (100% dichloromethane→95% dichloromethane/methanol) to give the title compound (1 g). MS 295.1 (M+1).

Provenance & Evidence