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

HRID 2261761
Notes
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Reaction equation

HRID 2261761 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 (100 mg, 0.394 mmol), potassium carbonate (163 mg, 1.18 mmol) and DMF 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, 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. stirringthe reaction is stirred for 30 minutes
  2. filtrationfiltered
  3. concentrationThe filtrate is concentrated under high vacuum
  4. additiondiluted with ethyl acetate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a72de9fa533f43fa9686719cd0178f1d
Source dataset
uspto-grants-2010_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07846960B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes