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Dimethylformamide → Methyl 6-bromo-1-methyl-1H-indole-3-carboxylate

HRID 250232
Notes
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Reaction equation

HRID 250232 reaction equation
COC(C1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([Br:14])[CH:12]=2)NC=1)=O.[C:15](=[O:18])([O-])[O-:16].[K+].[K+].[CH3:21][N:22]([CH:24]=O)[CH3:23].I[CH3:27]>ClCCl>[CH3:27][O:16][C:15]([C:13]1[C:8]2[C:21](=[CH:12][C:11]([Br:14])=[CH:10][CH:9]=2)[N:22]([CH3:23])[CH:24]=1)=[O:18]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodide2×HCID 11430Potassium CarbonateHCID 285091Methyl 5-bromo-1H-indole-3-carboxylate

Product 1

HCID 57443279Methyl 6-bromo-1-methyl-1H-indole-3-carboxylateYield 99%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

To a room temperature mixture of 5-bromo-1H-indole-3-carboxylic acid methyl ester (100 mg, 0.394 mmol), potassium carbonate (163 mg, 1.18 mmol) and DMF is added iodomethane (30 μL, 0.47 mmol). After 1.5 hours, additional iodomethane (10 μL) is added and the reaction is stirred for 30 minutes. The reaction mixture is diluted with dichloromethane and filtered. The filtrate is concentrated under high vacuum, diluted with ethyl acetate, and concentrated to give the title compound (105 mg, 99%). ES/MS m/e 270.0 (M+2).

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate is concentrated under high vacuum
  3. additiondiluted with ethyl acetate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-6fbca1a9bcb24dd8aadc869d45e4b873
Source dataset
uspto-grants-2011_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07863302B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes