Methyl iodide → Methyl N-methylindole-6-carboxylate

HRID 1622220Notes

Reaction equation

HRID 1622220 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:13]=[C:12]2[C:8]([CH:9]=[CH:10][NH:11]2)=[CH:7][CH:6]=1)=[O:4].[H-].[Na+].I[CH3:17]>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[CH:13]=[C:12]2[C:8]([CH:9]=[CH:10][N:11]2[CH3:17])=[CH:7][CH:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 639844Methyl indole-6-carboxylate

Product 1

HCID 639843Methyl N-methylindole-6-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of methyl-indole-6-caroxylate (3.0 g, 16.6 mmol), sodium hydride (1.0 g, 24.9 mmol), DMF (20 ml) was stirred for 1 h at room-temperature followed by addition of iodomethane (4.7 g, 33.2 mmol) and stirring at room-temperature for 15 h. The mixture was extracted with chloroform and evaporated. The product was isolated by evaporation. Yield 3.2 g (100%).

Workup

  1. stirringstirring at room-temperature for 15 h
  2. extractionThe mixture was extracted with chloroform
  3. customevaporated
  4. customThe product was isolated by evaporation

Sources & evidence

ORD record
ord-22b82ce7ccae4bd680f5670967d88396
Source dataset
uspto-grants-2014_07
Patent number
US08778928B2

Reaction notes

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