Cesium carbonate → 1-(cyclopropylmethyl)-5-(6-ethenyl-2-fluoropyridin-3-yl)-4-(trifluoromethyl)-1H-benzotriazole

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Reaction Steps

5-(6-Chloro-2-fluoropyridin-3-yl)-1-(cyclopropylmethyl)-4-(trifluoromethyl)-1H-benzotriazole (135 mg, 0.37 mmol) was dissolved in degassed tetrahydrofuran (3.3 mL) and treated with potassium trifluoro(vinyl)borate (174 mg, 1.3 mmol, 4 equiv), cesium carbonate (154 mg, 0.47 mmol, 1.3 equiv) and bis(tri-tert-butylphosphine)palladium(0) (56 mg, 0.11 mmol, 0.3 equiv). The mixture was placed into a preheated oil bath at 65° C. for 1.5 hours, cooled to ambient temperature, diluted with ethyl acetate (50 mL) and washed with sodium bicarbonate (2×30 mL, aqueous saturated). The combined organic extracts were dried with sodium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography (100% dichloromethane), providing the titled compound.

Provenance & Evidence