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

HRID 129518

반응식

HRID 129518 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-742de573106d4029966a3458d1fc3e2c
출처 데이터셋
uspto-grants-1995_11
특허 번호
US05468768

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