Ammonium formate → Ethyl 5-amino-1-ethyl-1H-indole-2-carboxylate

HRID 489988ノート

反応式

HRID 489988 の反応式
[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:18][CH3:19])[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([N+:15]([O-])=O)=[CH:10][CH:9]=2)=[O:5])[CH3:2].C([O-])=O.[NH4+]>CCO.C(O)CC.[OH-].[Pd+2].[OH-]>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:18][CH3:19])[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([NH2:15])=[CH:10][CH:9]=2)=[O:5])[CH3:2]

参加物

5

反応物 2

HCID 2723923Ammonium formateHCID 12148796ethyl 1-ethyl-5-nitro-1H-indole-2-carboxylate

生成物 1

HCID 12148797Ethyl 5-amino-1-ethyl-1H-indole-2-carboxylate収率 90.2%

試薬・触媒・溶媒 2

HCID 9942167Palladium hydroxide触媒HCID 9793718EtOH n-PrOH溶媒

実験手順

The 1-ethyl-5-nitro-1H-indole-2-carboxylic acid ethyl ester (5 g, 19.1 mmol) of step (a) was dissolved in EtOH/n-PrOH (100 mL, 1/1). Palladium hydroxide (1.14 g) and ammonium formate (3.92 g, 62.2 mmol) were added to the above solution. The mixture was heated to reflux for 2 hours. The reaction mixture was cooled to room temperature and the catalyst was filtered off through Celite. The solvent was removed under reduced pressure. The crude product was dissolved in dichloromethane (300 mL) and washed with NaHCO3 (150 ml×2). The organic layer was collected, dried (Na2SO4) and evaporated. The crude product was purified by chromatography to furnish the desired product (4 g, 90%).

後処理

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 2 hours
  3. filtrationthe catalyst was filtered off through Celite
  4. customThe solvent was removed under reduced pressure
  5. dissolutionThe crude product was dissolved in dichloromethane (300 mL)
  6. washwashed with NaHCO3 (150 ml×2)
  7. customThe organic layer was collected
  8. dry with materialdried (Na2SO4)
  9. customevaporated
  10. customThe crude product was purified by chromatography

出典と根拠

ORDレコード
ord-860473b917d3440c8123ddd457c26dfd
出典データセット
uspto-grants-2005_12
特許番号
US06979692B2

反応ノート

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