反应详情

200 mg of 6-bromo-N-phenylimidazo[1,2-a]pyridine-2-carboxamide (Intermediate 1), 10 mL of dioxane, 400 μL of 3-(triethoxysilyl)furan, 42 mg of palladium acetate, 42 mg of 1,4-diazabicyclo(2.2.2)octane (DABCO) and 1.5 mL of a molar solution of tetrabutylammonium fluoride in tetrahydrofuran are placed in a microwave tube. The reaction mixture is heated for 3 hours in a microwave machine set at 120° C., 200 μL of 3-(triethoxysilyl)furan, 20 mg of palladium acetate and 20 mg of DABCO are then added and the mixture is heated for a further 1.5 hours in a microwave machine set at 150° C. and then cooled and filtered. The filtrate is concentrated to dryness under reduced pressure and the residue is chromatographed on a silica cartridge, eluting with dichloromethane. The fractions containing the pure expected product are combined and evaporated to dryness under reduced pressure. The solid is dissolved while hot in a mixture of dichloromethane and methanol. The hot solution is filtered and treated with diisopropyl ether. The precipitate formed is filtered off by suction and dried to give 25 mg of 6-(3-furyl)-N-phenylimidazo[1,2-a]pyridine-2-carboxamide in the form of a yellow solid.

1. temperatureThe reaction mixture is heated for 3 hours in a microwave machine
2. customset at 120° C.
3. temperaturethe mixture is heated for a further 1.5 hours in a microwave machine
4. customset at 150° C.
5. temperaturecooled
6. filtrationfiltered
7. concentrationThe filtrate is concentrated to dryness under reduced pressure
8. customthe residue is chromatographed on a silica cartridge
9. washeluting with dichloromethane
10. additionThe fractions containing the pure expected product
11. customevaporated to dryness under reduced pressure
12. dissolutionThe solid is dissolved while
13. additionhot in a mixture of dichloromethane and methanol
14. filtrationThe hot solution is filtered
15. additiontreated with diisopropyl ether
16. customThe precipitate formed
17. filtrationis filtered off by suction
18. customdried