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Water → 1-Ethyl-3-{5-[(3-methyl-3H-imidazo[4,5-b]pyridin-2-yl)oxy]pyridin-2-yl}-1H-pyrazolo[4,3-b]pyridine

HRID 573326
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HRID 573326 반응식
[CH3:1][N:2]1[C:6]2=[N:7][CH:8]=[CH:9][CH:10]=[C:5]2[N:4]=[C:3]1S(C)(=O)=O.[CH2:15]([N:17]1[C:25]2[C:20](=[N:21][CH:22]=[CH:23][CH:24]=2)[C:19]([C:26]2[N:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=2)=[N:18]1)[CH3:16].[H-].[Na+].O>CN(C=O)C>[CH2:15]([N:17]1[C:25]2[C:20](=[N:21][CH:22]=[CH:23][CH:24]=2)[C:19]([C:26]2[CH:27]=[CH:28][C:29]([O:32][C:3]3[N:2]([CH3:1])[C:6]4=[N:7][CH:8]=[CH:9][CH:10]=[C:5]4[N:4]=3)=[CH:30][N:31]=2)=[N:18]1)[CH3:16]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

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HCID 962WaterHCID 24758Sodium hydrideHCID 585773713-Methyl-2-(methylsulfonyl)-3H-imidazo[4,5-b]pyridineHCID 1363976906-(1-Ethyl-1H-pyrazolo[4,3-b]pyridin-3-yl)pyridin-3-ol

생성물 1

HCID 667281201-Ethyl-3-{5-[(3-methyl-3H-imidazo[4,5-b]pyridin-2-yl)oxy]pyridin-2-yl}-1H-pyrazolo[4,3-b]pyridine수율 36.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
100 °C

실험 절차

To a mixture of 3-methyl-2-(methylsulfonyl)-3H-imidazo[4,5-b]pyridine (90 mg) and 6-(1-ethyl-1H-pyrazolo[4,3-b]pyridin-3-yl)pyridin-3-ol (68 mg) in DMF (1 mL) was added NaH (60% in oil, 18.11 mg), and the mixture was stirred at 100° C. for 1 h. The mixture was heated at 180° C. for 30 min under microwave irradiation. The mixture was poured into water and extracted with AcOEt. The organic layer was separated, washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (AcOEt/hexane). The eluent was evaporated and the residue was crystallized from EtOH/hexane to give the title compound (38.1 mg).

후처리

  1. temperatureThe mixture was heated at 180° C. for 30 min under microwave irradiation
  2. extractionextracted with AcOEt
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by basic silica gel column chromatography (AcOEt/hexane)
  8. customThe eluent was evaporated
  9. customthe residue was crystallized from EtOH/hexane

출처 및 근거

ORD 기록
ord-af457ea6be4b47148d654058b1651c55
출처 데이터셋
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09029536B2

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