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

HRID 129519Notes

Reaction equation

HRID 129519 reaction equation
[CH3:1][NH:2][C:3](=[O:18])[CH2:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9]([Si](C)(C)C)=[CH:8]2>CC#N>[CH3:1][NH:2][C:3](=[O:18])[CH2:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][CH:9]=[CH:8]2

Participants

3

Reactant 1

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

Product 1

HCID 15391297N-Methyl-1H-indole-5-acetamideYield 47.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N-Methyl-2-(trimethylsilyl)-1H-indole-5-acetamide (8) (2.5 g, 0.00961 mol) was dissolved in CH3CN (50 mL) and HF (1.9 g of a 50% aqueous solution, 0.048 mol) was added. The mixture was stirred at RT for 1.5 h. The solvent was removed in vacuo and the residue was dissolved in EtOAc. The organic phase was extracted with saturated aqueous NaHCO3 and then with brine, dried over MgSO4, filtered and evaporated in vacuo. Silica gel chromatography (10-100% EtOAc gradient in hexane) of the concentrate afforded the product (0.86 g, 47.6%).

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in EtOAc
  3. extractionThe organic phase was extracted with saturated aqueous NaHCO3
  4. dry with materialwith brine, dried over MgSO4
  5. filtrationfiltered
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-54e82cef3ef1468eabf3ad44cd6d3bff
Source dataset
uspto-grants-1995_11
Patent number
US05468768

Reaction notes

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