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

HRID 1080697Notes

Reaction equation

HRID 1080697 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-ace27e4c71df4622a88f9a2ac05afb34
Source dataset
uspto-grants-1996_12
Patent number
US05583149

Reaction notes

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