Water → 7-Bromo-1-methyl-1H-indole

HRID 2303286Notes

Reaction equation

HRID 2303286 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[CH:7]2.[C:11]([O-])([O-])=O.[K+].[K+].CI.O>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[N:9]([CH3:11])[CH:8]=[CH:7]2

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 27570207-Bromoindole

Product 1

HCID 219500697-Bromo-1-methyl-1H-indole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

7-Bromoindole(0.37 g, 1.9 mmol) was dissolved in dry DMF. K2CO3 (0.52 g, 3.8 mmol) and methyliodide (0.13 mL, 2.08 mmol) were added. The reaction was stirred at room temperature for 5 days, after which H2O (20 mL) was added, the water phase was extracted with Et2O (3×20 mL), and the combined organic phases were washed with brine, dried (MgSO4), filtered and concentrated in vacuo. The crude product was purified by chromatography, eluent EtOAc:petroleum ether 1:20 to give 7-bromo-1-methylindole as a crystalline compound.

Workup

  1. extractionthe water phase was extracted with Et2O (3×20 mL)
  2. washthe combined organic phases were washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by chromatography, eluent EtOAc:petroleum ether 1:20

Sources & evidence

ORD record
ord-6a6cc6f75170470bb4e4d880a3663fcf
Source dataset
uspto-grants-2002_08
Patent number
US06432962B1

Reaction notes

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