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

HRID 1688826ノート

反応式

HRID 1688826 の反応式
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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 9942167Palladium hydroxide触媒HCID 702Ethanol溶媒

反応条件

温度
80 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-7cf7b96b0d0f46dfb2f65a81036b10c3
出典データセット
uspto-grants-2012_04
特許番号
US08148383B2

反応ノート

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