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

HRID 1392762Notes

Reaction equation

HRID 1392762 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-085e8f43dfa8450798e34e7a06b28371
Source dataset
uspto-grants-2008_03
Patent number
US07342014B2

Reaction notes

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