Methyl iodide → 1-Methyl-4-methoxyl-7-bromoindole

HRID 2215793Notes

Reaction equation

HRID 2215793 reaction equation
[H-].[Na+].[O:3]([C:5]1[CH:13]=[CH:12][C:11]([Br:14])=[C:10]2[C:6]=1[CH:7]=[CH:8][NH:9]2)[CH3:4].[CH3:15]I>CN(C=O)C>[CH3:15][N:9]1[C:10]2[C:6](=[C:5]([O:3][CH3:4])[CH:13]=[CH:12][C:11]=2[Br:14])[CH:7]=[CH:8]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 36954997-Bromo-4-methoxy-1H-indole

Product 1

HCID 219499811-Methyl-4-methoxyl-7-bromoindole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of sodium hydride (60%, 0.23 g, 5.75 mmol) in DMF (18 mL) was added a solution of 4-methoxyl-7-bromoindole (1.1 g, 4.87 mmol) in DMF (2 mL). After 1 h at room temperature, the mixture was treated with methyl iodide (0.45 mL, 7.23 mmol) with cooling in an ice-water bath. The reaction mixture was allowed to warm up room temperature and stirred overnight. The reaction was quenched with water, extracted with ethyl acetate and the extract washed with water and brine, and dried (sodium sulfate). Evaporation of solvent gave a crude product, which was used without further purification. 1H NMR (400 MHz, CDCl3) 3.92(σ,3H), 4.13 (s, 3H), 6.35 (d, J=8.21 Hz, 1H), 6.55 (d, J=3.13 Hz, 1H), 6.89 (d, J=3.52 Hz, 1H), 7.22 (d, J=8.21 Hz, 1H).

Workup

  1. temperaturewith cooling in an ice-water bath
  2. customThe reaction was quenched with water
  3. extractionextracted with ethyl acetate
  4. washthe extract washed with water and brine
  5. dry with materialdried (sodium sulfate)
  6. customEvaporation of solvent

Sources & evidence

ORD record
ord-9c9ba635fe854fd29cb0ed39a84be8cd
Source dataset
uspto-grants-2006_09
Patent number
US07109229B2

Reaction notes

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