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

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Reaction Steps

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.

Provenance & Evidence