Methyl iodide → 7-Bromo-5-fluoro-1-methyl-1H-indole

HRID 2215789Notes

Reaction equation

HRID 2215789 reaction equation
[H-].[Na+].[F: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]([F:3])=[CH:12][C:11]=2[Br:13])[CH:7]=[CH:8]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 38528797-bromo-5-fluoro-1H-indole

Product 1

HCID 219500637-Bromo-5-fluoro-1-methyl-1H-indole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of sodium hydride (60%, 1.75 g, 43.8 mmol) in DMF (134 mL) was added a solution of 5-fluoro-7-bromoindole (7.8 g, 36.4 mmol) in DMF (10 mL). After 1 h at room temperature, the mixture was treated with methyl iodide (3.4 mL, 54.6 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 organic layer was washed with water and brine, dried (sodium sulfate) and concentrated to give a crude product, which was used without further purification. 1H NMR (400 MHz, CDCl3) 4.06 (s, 3H), 6.34 (d, J=3.13 Hz, 1H), 6.96 (d, J=3.13 Hz, 1H), 7.07 (dd, J1=2.34 Hz, J2=8.60 Hz, 1H), 7.12 (dd, J1=2.34 Hz, J2=9.0 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 organic layer was washed with water and brine
  5. dry with materialdried (sodium sulfate)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f968cbe16e6748b1bc6bcf5d7126b312
Source dataset
uspto-grants-2006_09
Patent number
US07109229B2

Reaction notes

Loading…