Methyl iodide → 4-Bromo-1-methyl-1H-indole

HRID 984710Notes

Reaction equation

HRID 984710 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.[H-].[Na+].CI.[C:15](OCC)(=O)C>CN(C=O)C>[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][N:6]2[CH3:15]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 6764944-Bromoindole

Product 1

HCID 225589374-Bromo-1-methyl-1H-indole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-bromoindole (5 g, TCI) in DMF (30 ml) was added with 60% sodium hydride (1.14 g) under ice cooling and stirred for 10 minutes. The mixture was added dropwise with methyl iodide (3.18 ml, TCI), stirred for 10 minutes, then warmed to room temperature and further stirred for 30 minutes. The reaction mixture was poured into ice water and added with ethyl acetate (300 ml) for extraction. The organic layer was washed successively with saturated aqueous sodium hydrogencarbonate, saturated aqueous ammonium chloride and saturated brine and dried, and then the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (Quad, hexane:ethyl acetate=10:1) to obtain the title compound (Intermediate 51, 4.95 g).

Workup

  1. stirringstirred for 10 minutes
  2. stirringfurther stirred for 30 minutes
  3. washThe organic layer was washed successively with saturated aqueous sodium hydrogencarbonate, saturated aqueous ammonium chloride and saturated brine
  4. customdried
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by column chromatography (Quad, hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-748f267cec1046d98f81aa62c1c7ef72
Source dataset
uspto-grants-2005_03
Patent number
US06867320B2

Reaction notes

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