反应详情

The 2-(4-chlorophenyl)-3H-imidazo[4,5-b]pyridine (2.29 g, 0.01 mole), was added to a suspension of sodium hydride (0.44 g of 60% sodium hydride/oil, 0.01 mole, washed once with hexanes) in 50 ml of dimethylformamide. The mixture was heated to 70° C. for 1 hr before the addition of chloroacetone (0.93 g, 0.01 mole) at room temperature. The reaction mixture was stirred at room temperature overnight, then poured into 300 ml of water. The precipitate was collected by filtration, washed with water, and dried under high vacuum at 50° C. overnight. The solid was recrystallized from methanol-water and dried under high vacuum at 50° C. overnight. The solid was dissolved in methanol, treated with charcoal, and filtered through Celite to give a pale yellow filtrate. The filtrate was concentrated and diluted with water to initiate crystallization. The precipitate was collected by filtration, washed with water, and dried under high vacuum overnight. The solid was dissolved in isopropyl alcohol, acidified with ethereal hydrogen chloride, diluted with isopropyl ether, and seeded to initiate crystallization. The crystalline solid was collected by filtration, washed with isopropyl ether, and under high vacuum overnight to give 1.6 g (50%), m.p. 220°-22° C.

1. washwashed once with hexanes) in 50 ml of dimethylformamide
2. filtrationThe precipitate was collected by filtration
3. washwashed with water
4. customdried under high vacuum at 50° C. overnight
5. customThe solid was recrystallized from methanol-water
6. customdried under high vacuum at 50° C. overnight
7. dissolutionThe solid was dissolved in methanol
8. additiontreated with charcoal
9. filtrationfiltered through Celite
10. customto give a pale yellow filtrate
11. concentrationThe filtrate was concentrated
12. additiondiluted with water
13. customcrystallization
14. filtrationThe precipitate was collected by filtration
15. washwashed with water
16. customdried under high vacuum overnight
17. dissolutionThe solid was dissolved in isopropyl alcohol
18. additiondiluted with isopropyl ether
19. customcrystallization
20. filtrationThe crystalline solid was collected by filtration
21. washwashed with isopropyl ether
22. customunder high vacuum overnight to give 1.6 g (50%), m.p. 220°-22° C.