Acetic Acid → N-(4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-1H-pyrazol-5-amine

HRID 1688826노트

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HRID 1688826 반응식
C([N:8]1[C:12]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22])=[CH:16][CH:15]=2)=[CH:11][CH:10]=[N:9]1)C1C=CC=CC=1.C(O)(=O)C.C([O-])=O.[NH4+].C(OCC)(=O)C>C(O)C.[OH-].[Pd+2].[OH-]>[Si:21]([O:20][C:17]1[CH:18]=[CH:19][C:14]([NH:13][C:12]2[NH:8][N:9]=[CH:10][CH:11]=2)=[CH:15][CH:16]=1)([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:22])[CH3:23]

참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 8857Ethyl AcetateHCID 2723923Ammonium formateHCID 670088731-benzyl-N-(4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-1H-pyrazol-5-amine

생성물 1

HCID 67009063N-(4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-1H-pyrazol-5-amine수율 74.9%

시약·촉매·용매 2

HCID 9942167Palladium hydroxide촉매HCID 702Ethanol용매

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온도
80 °C

실험 절차

To a suspension of 1-benzyl-N-(4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-1H-pyrazol-5-amine (4.9 g) and palladium hydroxide (10 wt %, 5.0 g) in ethanol (22.5 mL)-acetic acid (2.5 mL) was added ammonium formate (2.4 g) at 80° C. After stirring at 80° C. for 3 hr, the mixture was allowed to cool, ethyl acetate was added, and the insoluble material was filtered off. Saturated aqueous sodium hydrogen carbonate solution was added to the filtrate, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography to give the title compound as a pale-yellow amorphous solid (2.8 g, 74%).

후처리

  1. temperatureto cool
  2. filtrationthe insoluble material was filtered off
  3. additionSaturated aqueous sodium hydrogen carbonate solution was added to the filtrate
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with water and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-7cf7b96b0d0f46dfb2f65a81036b10c3
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08148383B2

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