Bis(trimethylsilyl)acetylene → N-Methyl-2-(trimethylsilyl)-1H-indole-5-acetamide

HRID 129518

反応式

HRID 129518 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([NH:11][CH3:12])=[O:10])=[CH:4][C:3]=1I.[CH3:14][Si:15]([C:18]#[C:19][Si](C)(C)C)([CH3:17])[CH3:16].C([O-])(O)=O.[Na+]>CC#N>[CH3:12][NH:11][C:9](=[O:10])[CH2:8][C:5]1[CH:4]=[C:3]2[C:2](=[CH:7][CH:6]=1)[NH:1][C:18]([Si:15]([CH3:17])([CH3:16])[CH3:14])=[CH:19]2

参加物

5

反応物 3

HCID 84564Bis(trimethylsilyl)acetyleneHCID 516892Sodium BicarbonateHCID 233658104-Amino-3-iodo-n-methylbenzeneacetamide

生成物 1

HCID 53754418N-Methyl-2-(trimethylsilyl)-1H-indole-5-acetamide収率 38.8%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

4-Amino-3-iodo-N-methyl-benzeneacetamide (7) (7.26 g, 0.025 mol), bis(trimethylsilyl) acetylene (8.52 g, 0.05 mol) and tetrakistriphenylphosphine Pd(O) (2.89 g, 0.0025 mol) were dissolved in CH3CN (400 mL) followed by the addition of saturated aqueous NaHCO3 (30 mL). The mixture was heated at reflux for 24 h. The solvent was removed in vacuo and the residue was dissolved in EtOAc. The organic phase was extracted with brine, dried over MgSO4, filtered and concentrated in vacuo. Silica gel chromatography (50-100% EtOAc gradient in hexane) of the concentrate afforded the product (8) (2.52 g, 38.8%) as a yellow viscous oil.

後処理

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 24 h
  3. customThe solvent was removed in vacuo
  4. dissolutionthe residue was dissolved in EtOAc
  5. extractionThe organic phase was extracted with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-742de573106d4029966a3458d1fc3e2c
出典データセット
uspto-grants-1995_11
特許番号
US05468768

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