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ChemicalBook CAS DataBase List 6-Chloroindole-2-carboxylic acid ethyl ester
27034-51-1

6-Chloroindole-2-carboxylic acid ethyl ester synthesis

13synthesis methods
-

Yield: 50%

Reaction Conditions:

with hydrogenchloride in glacial HOAc;ethanol;dichloromethane

Steps:

105.2 4-{2-[1-Benzhydryl-6-chloro-2-(2-phenylmethanesulfonylamino-ethyl)-1H-indol-3-yl]-ethoxy}-benzoic acid
Step 2: To crude 3-(4-chloro-2-nitro-phenyl)-2-oxo-propionic acid ethyl ester (151 mmol) in ethanol:glacial HOAc (1:1, v/v, 560 mL) at rt was added iron powder (74.4 g) and the reaction mixture was stirred at reflux for 4 h. The mixture was filtered and evaporated to give a residue which was redistributed in dichloromethane/1N HCl. The organic layer was washed with 1N HCl, NaHCO3, and brine and dried. Evaporation followed by crystallization (DCM) gave 6-Chloro-1H-indole-2-carboxylic acid ethyl ester as a pale yellow solid (16.8 g, 50% over 2 steps).

References:

Wyeth US2003/144282, 2003, A1

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