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

HRID 1080698Notes

Reaction equation

HRID 1080698 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-1768ce87b2b74b15866dcaef3fee5269
Source dataset
uspto-grants-1996_12
Patent number
US05583149

Reaction notes

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