Ethyl bromoacetate → HCID 10111629, compound

HRID 1007504Notes

Reaction equation

HRID 1007504 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([CH3:22])[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:1][C:2]1[CH:3]=[C:4]([NH:5][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH:6]=[C:7]([CH3:22])[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]([CH3:20])[CH3:21]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetate2×HCID 517045Sodium AcetateHCID 22669559HCID 22669559, compound

Product 1

HCID 10111629HCID 10111629, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

120 mg of 3-chloro-4-[(3-isopropyl-1H-indol-5-yl)oxy]-5-methylaniline (Example III) are heated to reflux with 62 mg of sodium acetate and 63 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 3 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 56 mg of ethyl N-{3-chloro-4-[(3-isopropyl-1H-indol-5-yl)oxy]-5-methylphenyl}glycinate.

Workup

  1. temperaturethe mixture is refluxed for 3 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-c23ce98e7e9c4975865f8e53322442d3
Source dataset
uspto-grants-2004_09
Patent number
US06794406B2

Reaction notes

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