Methyl iodide → 1,4-Dimethylindole

HRID 1047181Notes

Reaction equation

HRID 1047181 reaction equation
[CH3:1]I.C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:9][C:10]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:11]=1[CH:12]=[CH:13][NH:14]2>CN(C)C=O>[CH3:1][N:14]1[C:15]2[C:11](=[C:10]([CH3:9])[CH:18]=[CH:17][CH:16]=2)[CH:12]=[CH:13]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 852824-Methylindole

Product 1

HCID 5893891,4-DimethylindoleYield 85.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl iodide (28.44 g) and cesium carbonate (82.26 g) were added to a solution of 4-methylindole (22.08 g) in dimethylformamide (200 mL), and the reaction mixture was stirred at room temperature overnight. The reaction mixture was filtered with Celite (trade name), and the filtrate was concentrated under reduced pressure. A saturated aqueous solution of ammonium chloride was added to the obtained residue, and the reaction mixture was extracted with ethyl acetate. The obtained organic layer was washed with water and a saturated salt solution, and concentrated under reduced pressure after drying with anhydrous sodium sulfate. The obtained residue was purified by column chromatography on silica gel (hexane:ethyl acetate=100:0→85:15) to give the title compound (20.83 g) having the following physical data.

Workup

  1. filtrationThe reaction mixture was filtered with Celite (trade name)
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionA saturated aqueous solution of ammonium chloride was added to the obtained residue
  4. extractionthe reaction mixture was extracted with ethyl acetate
  5. washThe obtained organic layer was washed with water
  6. concentrationa saturated salt solution, and concentrated under reduced pressure
  7. dry with materialafter drying with anhydrous sodium sulfate
  8. customThe obtained residue was purified by column chromatography on silica gel (hexane:ethyl acetate=100:0→85:15)

Sources & evidence

ORD record
ord-59d34a16f19646c495e36ee6ee4f785c
Source dataset
uspto-grants-2013_10
Patent number
US08569504B2

Reaction notes

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