反应详情

温度

80 °C

To a solution of 8-bromo-7-chloro-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one (515 mg, 2.258 mmol) in anhydrous DMF (10 mL) was added 5-(chloromethyl)-2-(trifluoromethyl)pyridine (883 mg, 4.518 mmol), followed by solid potassium carbonate (624 mg, 4.518 mmol). The resulting suspension was stirred under argon at 80° C. for 1.5 h. After cooling to room temperature, the reaction mixture was partitioned between EtOAc and water, and the aqueous layer was extracted with EtOAc twice. The combined EtOAc extracts were washed with water, then saturated aqueous NaCl, dried over Na2SO4, and evaporated under reduced pressure to provide crude product as a brown solid. The crude product was purified by silica gel (40 g) column chromatography eluting with a gradient of EtOAc (0-60%) in hexanes to obtain the title compound as a beige solid (742 mg, 81%). HPLC/MS: retention time=3.17 min, [M+H]+=407. See 7,8-bis(4-chlorophenyl)-2-((6-(trifluoromethyl)pyridin-3-yl)methyl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one for data addressing the question of N vs. O-alkylation.

1. temperatureAfter cooling to room temperature
2. customthe reaction mixture was partitioned between EtOAc and water
3. extractionthe aqueous layer was extracted with EtOAc twice
4. washThe combined EtOAc extracts were washed with water
5. dry with materialsaturated aqueous NaCl, dried over Na2SO4
6. customevaporated under reduced pressure
7. customto provide crude product as a brown solid
8. customThe crude product was purified by silica gel (40 g) column chromatography
9. washeluting with a gradient of EtOAc (0-60%) in hexanes