Dimethylformamide → 6-Bromo-1-methyl-1H-indole

HRID 268828Notes

Reaction equation

HRID 268828 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][CH:3]=1.[H-].[Na+].[CH3:13]N(C=O)C>>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][N:8]2[CH3:13])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 6764936-Bromoindole

Product 1

HCID 155468546-Bromo-1-methyl-1H-indole

Procedure

To a solution of 6-bromo-1H-indole (2.5 g, 12.8 mmol) in DMF (10 ml) was slowly added NaH (354 mg, 14.0 mmol) at room temperature. The resulting mixture was stirred for 20 min at RT after which Mel (956 μl, 15.4 mmol) was added. The mixture was stirred for 1 hour at room temperature and then partitioned between DCM and brine. The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated to provide 6-Bromo-1-methyl-1H-indole CXLII in quantitative yield (2.7 g).

Workup

  1. customat room temperature
  2. additionwas added
  3. stirringThe mixture was stirred for 1 hour at room temperature
  4. custompartitioned between DCM and brine
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-6b9cb9af2a2644dc954c7b29e6607a19
Source dataset
uspto-grants-2008_11
Patent number
US07446118B2

Reaction notes

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