Methyl iodide → 5-Bromo-1-methyl-1H-indole

HRID 2405330Notes

Reaction equation

HRID 2405330 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.[OH-].[Na+].[CH3:13]I>CS(C)=O.O>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:13])[CH:6]=[CH:5]2

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 249055-Bromoindole

Product 1

HCID 2857575-Bromo-1-methyl-1H-indole

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A solution of 5-bromo-1H-indole (1.530 mmol) in dimethyl sulfoxide (10 mL) was treated with NaOH (2.295 mmol) and stirred at room temperature for 30 min. The solution was then treated with methyl iodide (4.59 mmol) and was stirred for 3 days at room temperature. The solution was diluted with water (100 mL) and was extracted with ethyl acetate. The combined organic phases were washed with water, washed with brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The yellow oil was used without further purification. MS(ES)+ m/e 210/212 [M+H]+ (bromide isotope pattern).

Workup

  1. stirringwas stirred for 3 days at room temperature
  2. extractionwas extracted with ethyl acetate
  3. washThe combined organic phases were washed with water
  4. washwashed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe yellow oil was used without further purification

Sources & evidence

ORD record
ord-e5b898e4ced74ed59ed5e252fc239640
Source dataset
uspto-grants-2014_08
Patent number
US08802864B2

Reaction notes

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