反应详情

温度

80 °C

An oven dried tube was charged with palladium acetate (0.20 g, 0.89 mmol) and triphenylphosphine (0.60 g, 2.3 mmol). The tube was evacuated under high vacuum and backflushed under a stream of nitrogen for 5 minutes. 1,4-Dioxane (10 mL) was added and the mixture was stirred under nitrogen for 10 minutes. 8-Bromo-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine (1.0 g, 4.7 mmol), 2-methoxybenzeneboronic acid (1.1 g, 7.0 mmol), N,N-dimethylformamide (10 mL) and 1.50 M of sodium carbonate in water (10 mL) were added. The mixture was stirred for 2 minutes at room temperature under nitrogen then the tube was sealed and heated at 80° C. for 18 hours. The mixture was transferred to a round bottom flask and the volatiles were evaporated under reduced pressure. Water (100 mL) was added and the mixture was stirred when a precipitate was formed. The solid was collected by filtration, rinsed with water, air dried, triturated with ether/dichloromethane (4:1; 10 mL), filtered and rinsed with ether. 8-(2-Methoxy-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine was isolated (1.0 g, 89%). 1H NMR (400 MHz, CDCl3, δ, ppm): 8.50 (d, J=6.5 Hz, 1H), 7.51 (dd, J=7.6, 1.5 Hz, 1H), 7.43-7.36 (m, 2H), 7.13 (d, J=8.1 Hz, 1H), 7.02 (t, J=7.3 Hz, 1H), 6.91 (t, J=7.0 Hz, 1H), 5.96 (br s, 2H), 3.73 (s, 3H). MS=241 (MH)+.

1. customAn oven dried tube
2. customThe tube was evacuated under high vacuum
3. addition1,4-Dioxane (10 mL) was added
4. stirringThe mixture was stirred for 2 minutes at room temperature under nitrogen
5. customthe tube was sealed
6. customThe mixture was transferred to a round bottom flask
7. customthe volatiles were evaporated under reduced pressure
8. additionWater (100 mL) was added
9. stirringthe mixture was stirred when a precipitate
10. customwas formed
11. filtrationThe solid was collected by filtration
12. washrinsed with water, air
13. customdried
14. customtriturated with ether/dichloromethane (4:1; 10 mL)
15. filtrationfiltered
16. washrinsed with ether