Dabco → 6-(3-furyl)-N-phenylimidazo[1,2-a]pyridine-2-carboxamide

HRID 2363705

Reaktionsgleichung

Reaktionsgleichung von HRID 2363705
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]([NH:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[O:12])[N:10]=2)[CH:7]=1.C(O[Si](OCC)(OCC)[C:24]1[CH:28]=[CH:27][O:26][CH:25]=1)C.N12CCN(CC1)CC2.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O1CCOCC1>[O:26]1[CH:27]=[CH:28][C:24]([C:2]2[CH:3]=[CH:4][C:5]3[N:6]([CH:8]=[C:9]([C:11]([NH:13][C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)=[O:12])[N:10]=3)[CH:7]=2)=[CH:25]1

Komponenten

8

Edukt 4

HCID 9237Dabco2×HCID 2724141Tetrabutylammonium FluorideHCID 12556749Triethoxy(furan-3-yl)silane2×HCID 247716736-bromo-N-phenylimidazo[1,2-a]pyridine-2-carboxamide2×

Produkt 1

HCID 441377666-(3-furyl)-N-phenylimidazo[1,2-a]pyridine-2-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysator2×HCID 8028TetrahydrofuranLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-46d882a1d08c4733a9540da3f17e17e4
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08691990B2

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