Benzene → ethyl 3-bromo-5-formyl-1-isobutyl-1H-indole-2-carboxylate

HRID 2249693Notes

Reaction equation

HRID 2249693 reaction equation
[CH2:1]([N:5]1C2C(=CC(C)=CC=2)[CH:7]=[C:6]1[C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:2]([CH3:4])[CH3:3].[Br:20]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N.[C:40]([O-:43])(=O)C.[K+].[CH:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1>CN(C)C=O.O.C(OCC)(=O)C>[Br:20][C:7]1[C:50]2[C:45](=[CH:46][CH:47]=[C:48]([CH:40]=[O:43])[CH:49]=2)[N:5]([CH2:1][CH:2]([CH3:4])[CH3:3])[C:6]=1[C:15]([O:17][CH2:18][CH3:19])=[O:16]

Participants

9

Reactant 5

HCID 241BenzeneHCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 517044Potassium AcetateHCID 17816463ethyl 1-isobutyl-5-methyl-1H-indole-2-carboxylate

Product 1

HCID 17816525ethyl 3-bromo-5-formyl-1-isobutyl-1H-indole-2-carboxylate

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
40 °C

Procedure

In 10 ml of benzene are suspended 1.00 g of ethyl 1-isobutyl-5-methyl-1H-indole-2-carboxylate, 0.76 g of N-bromosuccinimide and 0.07 g of 2,2′-azobisisobutyronitrile. The suspension is heated under reflux for two hours. The reaction mixture is concentrated under reduced pressure, and the residue thus obtained is dissolved in 10 ml of N,N-dimethylformamide. After adding 0.57 g of potassium acetate, the mixture is stirred at 40° C. for 30 minutes. The reaction mixture is added to a mixture of ethyl acetate and water, and the organic layer is separated. The organic layer thus obtained is washed with water and saturated aqueous solution of sodium chloride successively and dried over anhydrous magnesium sulfate, and then the solvent is distilled off under reduced pressure. The residue thus obtained is purified by silica gel column chromatography (eluent; hexane:ethyl acetate=6:1) to obtain 0.68 g of ethyl 3-bromo-5-formyl-1-isobutyl-1H-indole-2-carboxylate as a yellow oily product.

Workup

  1. temperatureThe suspension is heated
  2. temperatureunder reflux for two hours
  3. concentrationThe reaction mixture is concentrated under reduced pressure
  4. customthe residue thus obtained
  5. customthe organic layer is separated
  6. customThe organic layer thus obtained
  7. washis washed with water and saturated aqueous solution of sodium chloride successively
  8. dry with materialdried over anhydrous magnesium sulfate
  9. distillationthe solvent is distilled off under reduced pressure
  10. customThe residue thus obtained
  11. customis purified by silica gel column chromatography (eluent; hexane:ethyl acetate=6:1)

Sources & evidence

ORD record
ord-16e1ec2c4e07447c8492ba88ec119171
Source dataset
uspto-grants-2008_01
Patent number
US07314888B1

Reaction notes

Loading…