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Isopropanol → 4-(1-Ethyl-6-fluoro-1H-pyrazolo[4,3-b]pyridin-3-yl)phenol

HRID 573341
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HRID 573341 반응식
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([C:17]2[C:22](F)=[CH:21][C:20]([F:24])=[CH:19][N:18]=2)=O)=[CH:11][CH:10]=1)C1C=CC=CC=1.[CH2:25]([NH:27][NH2:28])[CH3:26].CC(O)C>O>[CH2:25]([N:27]1[C:22]2[C:17](=[N:18][CH:19]=[C:20]([F:24])[CH:21]=2)[C:15]([C:12]2[CH:11]=[CH:10][C:9]([OH:8])=[CH:14][CH:13]=2)=[N:28]1)[CH3:26]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 3776IsopropanolHCID 29062EthylhydrazineHCID 66727888[4-(Benzyloxy)phenyl](3,5-difluoropyridin-2-yl)methanone

생성물 1

HCID 1363976944-(1-Ethyl-6-fluoro-1H-pyrazolo[4,3-b]pyridin-3-yl)phenol수율 69.5%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A mixture of [4-(benzyloxy)phenyl](3,5-difluoropyridin-2-yl)methanone (400 mg), ethylhydrazine (369 mg) and 2-propanol (5 mL) was stirred at room temperature for 30 min, and at 90° C. for 12 h, treated with water, and extracted with AcOEt. The organic layer was dried over MgSO4 and concentrated under reduced pressure. The residue was dissolved in EtOH (40 mL) and 10% Pd—C (50% wet, 400 mg) was added. The mixture was stirred at room temperature for 1 h under H2 atmosphere, filtered and evaporated. The residue was suspended in AcOEt/IPE and collected by filtration to give the title compound (220 mg).

후처리

  1. waitat 90° C. for 12 h
  2. extractionextracted with AcOEt
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe residue was dissolved in EtOH (40 mL)
  6. addition10% Pd—C (50% wet, 400 mg) was added
  7. stirringThe mixture was stirred at room temperature for 1 h under H2 atmosphere
  8. filtrationfiltered
  9. customevaporated
  10. filtrationcollected by filtration

출처 및 근거

ORD 기록
ord-213f231760d942f5ae48c884aa9b67fe
출처 데이터셋
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09029536B2

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