N-bromobutanimide → Ethyl 3-bromo-5-chloro-1H-indole-2-carboxylate

HRID 902868Notes

Reaction equation

HRID 902868 reaction equation
[Br:1]N1C(=O)CCC1=O.[Cl:9][C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[NH:15][C:14]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:13]2>CN(C)C=O>[Br:1][C:13]1[C:12]2[C:16](=[CH:17][CH:18]=[C:10]([Cl:9])[CH:11]=2)[NH:15][C:14]=1[C:19]([O:21][CH2:22][CH3:23])=[O:20]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 78518Ethyl 5-chloroindole-2-carboxylate

Product 1

HCID 13466333Ethyl 3-bromo-5-chloro-1H-indole-2-carboxylateYield 100.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-Bromosuccinimide (440 mg) was added to a solution of ethyl 5-chloroindole-2-carboxylate (500 mg) in N,N-dimethylformamide (10 ml). The reaction mixture was stirred at room temperature for 18 hours, and the solvent was distilled off under reduced pressure. The residue was partitioned in ethyl acetate and water, and a water layer was extracted with ethyl acetate. The resultant organic layers were combined, washed with saturated aqueous solution of sodium chloride and then dried over anhydrous sodium sulfate. The solvent was distilled off, the residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:9), and white powder thus obtained was washed with hexane to obtain the title compound (680 mg).

Workup

  1. distillationthe solvent was distilled off under reduced pressure
  2. customThe residue was partitioned in ethyl acetate
  3. extractionwater, and a water layer was extracted with ethyl acetate
  4. washwashed with saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off
  7. customthe residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:9), and white powder
  8. customthus obtained
  9. washwas washed with hexane

Sources & evidence

ORD record
ord-f572e1e6ee054bc7b7ce542075dceae4
Source dataset
uspto-grants-2008_04
Patent number
US07365205B2

Reaction notes

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