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

HRID 1878453

반응식

HRID 1878453 반응식
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

참가 물질

8

반응물 4

HCID 9237Dabco2회HCID 2724141Tetrabutylammonium FluorideHCID 12556749Triethoxy(furan-3-yl)silane2회HCID 247716736-bromo-N-phenylimidazo[1,2-a]pyridine-2-carboxamide2회

생성물 1

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

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매2회HCID 8028Tetrahydrofuran용매HCID 312751,4-Dioxane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-ce98175516da4fbc82cfa42542ce9d89
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08314109B2

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