Ethanol → Ethyl 6-chloro-1-methyl-1H-indole-2-carboxylate

HRID 1280397Notes

Reaction equation

HRID 1280397 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[C:9]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[NH:10]2)=[CH:6][CH:5]=1.IC.[CH2:20](O)C>CN(C)C=O>[Cl:3][C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[C:9]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[N:10]2[CH3:20])=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 7015027Ethyl 6-chloroindole-2-carboxylate

Product 1

HCID 10561874Ethyl 6-chloro-1-methyl-1H-indole-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 1.8 g (45 mmol) of 60% sodium hydride (washed beforehand with petroleum ether) and of 8.0 g (35.8 mmol) of ethyl 6-chloro-1H-indole-2-carboxylate in 80 ml of N,N-dimethylformamide is stirred for 2 h at room temperature, 2.8 ml (45 mmol) of iodomethane are subsequently added and the mixture is stirred at room temperature for 4 h. 5 ml of absolute ethanol are added and the solvent is evaporated under reduced pressure. The residue is taken up in water and the mixture is extracted with dichloromethane, the organic phase is dried and filtered, the solvent is evaporated under reduced pressure and the residue is purified by chromatography on a column of silica gel. 8.5 g (35.7 mmol) of a white crystalline compound are isolated.

Workup

  1. customthe solvent is evaporated under reduced pressure
  2. extractionthe mixture is extracted with dichloromethane
  3. customthe organic phase is dried
  4. filtrationfiltered
  5. customthe solvent is evaporated under reduced pressure
  6. customthe residue is purified by chromatography on a column of silica gel

Sources & evidence

ORD record
ord-74dd2f5c6d6c404b812efa3add7dc317
Source dataset
uspto-grants-2002_09
Patent number
US06451795B1

Reaction notes

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