Methyl iodide → 1,5-Dimethyl-7-bromoindole

HRID 2215780

Reaction equation

HRID 2215780 reaction equation
[H-].[Na+].[CH3:3][C:4]1[CH:5]=[C:6]2[C:10](=[C:11]([Br:13])[CH:12]=1)[NH:9][CH:8]=[CH:7]2.[CH3:14]I>CN(C=O)C>[CH3:14][N:9]1[C:10]2[C:6](=[CH:5][C:4]([CH3:3])=[CH:12][C:11]=2[Br:13])[CH:7]=[CH:8]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 34033307-Bromo-5-methyl-1H-indole

Product 1

HCID 219499621,5-Dimethyl-7-bromoindoleYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of sodium hydride (60%, 0.91 g, 22.9 mmol) in DMF (70 mL) was added a solution of 5-methyl-7-bromoindole (4.0 g, 19.05 mmol) in DMF (10 mL). The mixture was stirred at room temperature for 1 h, and then methyl iodide (1.78 mL, 28.6 mmol) was added with cooling in an ice-water-bath. The reaction mixture was allowed to warm to room temperature and stirred overnight. The reaction was quenched with water and extracted with ethyl acetate. The extract was washed with water and brine, dried (sodium sulfate) and concentrated to give a crude product (4.1 g, 96%), which was used without further purification. 1H NMR (400 MHz, CDCl3) δ 2.38 (s, 3H), 4.12 (s, 3H), 6.36 (d, J=3.12 Hz, 1H), 6.95 (d, J=3.13 Hz, 1H), 7.18 (d, J=1.56 Hz, 1H), 7.31 (dd, J1=0.79 Hz, J2=1.56 Hz, 1H).

Workup

  1. temperaturewith cooling in an ice-water-bath
  2. temperatureto warm to room temperature
  3. stirringstirred overnight
  4. customThe reaction was quenched with water
  5. extractionextracted with ethyl acetate
  6. washThe extract was washed with water and brine
  7. dry with materialdried (sodium sulfate)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-12bc21d35cd446ed8b153ecd0cccc676
Source dataset
uspto-grants-2006_09
Patent number
US07109229B2

Linked notes

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