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

HRID 2104395Notes

Reaction equation

HRID 2104395 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH2:9]([O:11][C:12]([C:14]1[NH:15][C:16]2[C:21]([CH:22]=1)=[CH:20][C:19]([Cl:23])=[CH:18][CH:17]=2)=[O:13])[CH3:10]>CN(C)C=O>[CH2:9]([O:11][C:12]([C:14]1[NH:15][C:16]2[C:21]([C:22]=1[Br:1])=[CH:20][C:19]([Cl:23])=[CH:18][CH:17]=2)=[O:13])[CH3:10]

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 5-chloroindole-2-carboxylic acid ethyl ester (500 mg) in N,N-dimethylformamide (10 mL) under ice cooling. The reaction mixture was stirred at room temperature for 18 hours, and the solvent was distilled away under reduced pressure. The residue was partitioned between ethyl acetate and water. The aqueous layer was extracted with ethyl acetate, and the organic layers were combined. The combined organic layer was washed with saturated brine, and was dried over sodium sulfate anhydrate. The solvent was distilled away, and the residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:9). The thus-obtained white powder was washed with hexane, to thereby give the title compound (680 mg).

Workup

  1. distillationthe solvent was distilled away under reduced pressure
  2. customThe residue was partitioned between ethyl acetate and water
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. washThe combined organic layer was washed with saturated brine
  5. dry with materialwas dried over sodium sulfate anhydrate
  6. distillationThe solvent was distilled away
  7. customthe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:9)
  8. washThe thus-obtained white powder was washed with hexane

Sources & evidence

ORD record
ord-4507410c16b24462b568fc213aabd5c6
Source dataset
uspto-grants-2009_08
Patent number
US07576135B2

Reaction notes

Loading…