Sodium hydride → HCID 68504879, compound

HRID 1716421Notes

Reaction equation

HRID 1716421 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:13]2[C:8](=[CH:9][C:10]([Cl:14])=[CH:11][CH:12]=2)[NH:7][CH:6]=1)=[O:4].[H-].[Na+].Cl.Cl[CH2:19][CH2:20][N:21]([CH3:23])[CH3:22]>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[C:13]2[C:8](=[CH:9][C:10]([Cl:14])=[CH:11][CH:12]=2)[N:7]([CH2:19][CH2:20][N:21]([CH3:23])[CH3:22])[CH:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 49108265Methyl 6-chloro-1H-indole-3-carboxylate

Product 1

HCID 68504879HCID 68504879, compoundYield 35.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 80 mg (0.38 mol) of 6-chloro-1H-indole-3-carboxylic acid methyl ester in 5 ml of DMF were added 50 mg of NaH (3 eq, 55H in oil) at RT. After 20 min, 66 mg (0.45 mmol, 1.2 eq.) of (2-chloro-ethyl)-dimethyl-amine hydrochloride were added and stirring was continued overnight at 60° C. Extraction with EtOAc/aq. NH4Cl followed by flash chromatography yielded 45 mg of crude 6-chloro-1-(2-dimethylamino-ethyl)-1H-indole-3-carboxylic acid methyl ester.

Workup

  1. waitwas continued overnight at 60° C
  2. extractionExtraction with EtOAc/aq

Sources & evidence

ORD record
ord-24da12edf3e74f25be93752db0a3f05e
Source dataset
uspto-grants-2010_09
Patent number
US07803815B2

Reaction notes

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