Ethyl bromoacetate → ethyl N-{3,5-dichloro-4-[(3-isopropyl-1H-indol-5-yl)oxy]phenyl}glycinate

HRID 1007505Notes

Reaction equation

HRID 1007505 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([Cl:22])[C:8]=1[O:9][C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[NH:15][CH:14]=[C:13]2[CH:19]([CH3:21])[CH3:20])[NH2:5].C([O-])(=O)C.[Na+].Br[CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31]>C(O)C>[Cl:22][C:7]1[CH:6]=[C:4]([NH:5][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH:3]=[C:2]([Cl:1])[C:8]=1[O:9][C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[NH:15][CH:14]=[C:13]2[CH:19]([CH3:20])[CH3:21]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetate2×HCID 517045Sodium AcetateHCID 22669713HCID 22669713, compound

Product 1

HCID 10180486ethyl N-{3,5-dichloro-4-[(3-isopropyl-1H-indol-5-yl)oxy]phenyl}glycinateYield 17.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

100 mg of 3,5-dichloro-4-[(3-isopropyl-1H-indol-5-yl)oxy]aniline (Example IV) are heated to reflux with 49 mg of sodium acetate and 50 mg of ethyl bromoacetate in 5 ml of ethanol for 17 hours. A further 21 mg of ethyl bromoacetate are added and the mixture is refluxed for 2 hours. The solvent is removed in vacuo, the residue is taken up with water and dichloromethane, the organic phase is washed with saturated sodium chloride solution, dried and the solvent is removed in vacuo. Chromatographic purification (cyclohexane/ethyl acetate) affords 22 mg of ethyl N-{3,5-dichloro-4-[(3-isopropyl-1H-indol-5-yl)oxy]phenyl}glycinate.

Workup

  1. temperaturethe mixture is refluxed for 2 hours
  2. customThe solvent is removed in vacuo
  3. washthe organic phase is washed with saturated sodium chloride solution
  4. customdried
  5. customthe solvent is removed in vacuo
  6. customChromatographic purification (cyclohexane/ethyl acetate)

Sources & evidence

ORD record
ord-3a60aca6d36449fca2d40edece9c31dc
Source dataset
uspto-grants-2004_09
Patent number
US06794406B2

Reaction notes

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