Water → 1-Ethyl-3-[4-(3H-imidazo[4,5-b]pyridin-2-yloxy)phenyl]-1H-pyrazolo[4,3-b]pyridine

HRID 573295노트

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HRID 573295 반응식
[CH2:1]([N:3]1[C:11]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]2[CH:17]=[CH:16][C:15]([O:18][C:19]3[N:27](COCC[Si](C)(C)C)[C:22]4=[N:23][CH:24]=[CH:25][CH:26]=[C:21]4[N:20]=3)=[CH:14][CH:13]=2)=[N:4]1)[CH3:2].CCCC[N+](CCCC)(CCCC)CCCC.[F-].O>C1COCC1>[CH2:1]([N:3]1[C:11]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]2[CH:17]=[CH:16][C:15]([O:18][C:19]3[NH:27][C:22]4=[N:23][CH:24]=[CH:25][CH:26]=[C:21]4[N:20]=3)=[CH:14][CH:13]=2)=[N:4]1)[CH3:2]

참가 물질

5

반응물 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 667281621-ethyl-3-[4-(3-{[2-(trimethylsilyl)ethoxy]methyl}-3H-imidazo[4,5-b]pyridin-2-yloxy)phenyl]-1H-pyrazolo[4,3-b]pyridine

생성물 1

HCID 1784630051-Ethyl-3-[4-(3H-imidazo[4,5-b]pyridin-2-yloxy)phenyl]-1H-pyrazolo[4,3-b]pyridine수율 27.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
100 °C

실험 절차

A mixture of 1-ethyl-3-[4-(3-{[2-(trimethylsilyl)ethoxy]methyl}-3H-imidazo[4,5-b]pyridin-2-yloxy)phenyl]-1H-pyrazolo[4,3-b]pyridine (90 mg), 1 M TBAF in THF (0.74 mL) and THF (2 ml) was heated at 100° C. for 3 h under microwave irradiation. The mixture was stirred at 80° C. overnight. The mixture was poured into water and extracted with AcOEt. The organic layer was washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (AcOEt/hexane) to give the title compound (18 mg).

후처리

  1. extractionextracted with AcOEt
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by basic silica gel column chromatography (AcOEt/hexane)

출처 및 근거

ORD 기록
ord-5cb2fbe52a004876ae7166147f824a1c
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09029536B2

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