反应详情

温度

80 °C

To a solution of 4-(8-bromo-3-oxo-2,3-dihydro-[1,2,4]triazolo[4,3-a]pyridin-7-yl)benzonitrile (510 mg, 1.81 mmol) and 3-(chloromethyl)-2-methyl-6-(trifluoromethyl)pyridine (455 mg, 2.17 mmol) in anhydrous DMF (8 mL) was added anhydrous potassium carbonate (499 mg, 3.62 mmol). The resulting suspension was stirred under argon at 80° C. for 2 h. Analysis by HPLC/MS indicated the reaction was not complete. Additional of 3-(chloromethyl)-2-methyl-6-(trifluoromethyl)pyridine (120 mg, 0.57 mmol) and anhydrous potassium carbonate (200 mg, 2.07 mmol) were added, and the reaction mixture was stirred at 85° C. for 6 h more. After cooling to room temperature, the reaction mixture was partitioned between EtOAc and water, and the aqueous layer was extracted with EtOAc. The combined EtOAc extracts were washed with saturated aqueous NaCl, dried over Na2SO4, and concentrated under reduced pressure to afford a light brown solid. The solid was suspended in EtOAc/hexanes (about 1:1 ratio), then sonicated for 10 min to obtain a fine suspension. After filtration, the collected solid was washed with hexanes and dried in air to afford 500 mg of the title compound as a yellow solid. HPLC/MS: retention time=3.44 min, [M+H]+=489.2.

1. stirringthe reaction mixture was stirred at 85° C. for 6 h more
2. temperatureAfter cooling to room temperature
3. customthe reaction mixture was partitioned between EtOAc and water
4. extractionthe aqueous layer was extracted with EtOAc
5. washThe combined EtOAc extracts were washed with saturated aqueous NaCl
6. dry with materialdried over Na2SO4
7. concentrationconcentrated under reduced pressure
8. customto afford a light brown solid
9. customsonicated for 10 min
10. customto obtain a fine suspension
11. filtrationAfter filtration
12. washthe collected solid was washed with hexanes
13. customdried in air