N-amino-2-(1-butynyl)pyridinium mesitylenesulfonate → 2-Ethylpyrazolo[1,5-a]pyridine

HRID 9180노트

반응식

HRID 9180 반응식
C1(C)C=C(C)C=C(C)C=1S([O-])(=O)=O.[NH2:14][N+:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[C:21]#[C:22][CH2:23][CH3:24].CC(C)([O-])C.[K+]>O1CCCC1>[CH2:23]([C:22]1[CH:21]=[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][N:15]2[N:14]=1)[CH3:24]

참가 물질

4

반응물 2

HCID 21984654N-amino-2-(1-butynyl)pyridinium mesitylenesulfonateHCID 23665647Potassium tert-butoxide

생성물 1

HCID 161162612-Ethylpyrazolo[1,5-a]pyridine

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A 6.1 g portion of the obtained N-amino-2-(1-butynyl)pyridinium mesitylenesulfonate was dissolved in tetrahydrofuran (600 mL), potassium tert-butoxide (3.55 g) was added at room temperature, and the mixture was vigorously stirred for 30 minutes. After adding ice water to the reaction mixture, extraction was performed with ethyl acetate. The aqueous layer was again extracted with ethyl acetate, the insoluble portion was filtered with a celite filter, and the organic layers were combined and washed with brine. After drying over anhydrous magnesium sulfate and filtration, the solvent was concentrated under reduced pressure, the residue was purified by silica gel column chromatography, and the title compound (0.63 g) was obtained from the n-hexane:ethyl acetate (10:1) fraction as a light yellow oil.

후처리

  1. extractionto the reaction mixture, extraction
  2. extractionThe aqueous layer was again extracted with ethyl acetate
  3. filtrationthe insoluble portion was filtered with a celite
  4. filtrationfilter
  5. washwashed with brine
  6. dry with materialAfter drying over anhydrous magnesium sulfate and filtration
  7. concentrationthe solvent was concentrated under reduced pressure
  8. customthe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-e2417cce65cb4c1590485a0406f53f9b
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091215B2

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