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

HRID 250230
Notes
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Reaction equation

HRID 250230 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

A mixture of 5-bromo-1H-indole-3-carboxylic acid methyl ester (200 mg, 0.787 mmol), potassium carbonate (100 mg, 0.394 mmol) and DMF (1 mL) is stirred at room temperature and iodomethane (30 μL, 0.47 mmol) is added. After 1.5 hours, additional iodomethane (10 μL) is added and the reaction is stirred for 30 minutes and diluted with dichloromethane and filtered. The filtrate is concentrated under high vacuum, diluted with ethyl acetate, filtered and concentrated under reduced pressure to give the title compound (1105 mg, 99%). ES/MS m/e 270.0 (M+2).

Workup

  1. stirringthe reaction is stirred for 30 minutes
  2. filtrationfiltered
  3. concentrationThe filtrate is concentrated under high vacuum
  4. additiondiluted with ethyl acetate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9f1076a93477489685482a774718285f
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