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

6-Chloroindole-2-carboxylic acid ethyl ester synthesis

13synthesis methods

Product Name:6-Chloroindole-2-carboxylic acid ethyl ester
CAS Number:27034-51-1
Molecular formula:C11H10ClNO2
Molecular Weight:223.66

2-Propenoic acid, 2-azido-3-(4-chlorophenyl)-, ethyl ester, (2Z)-

24513-05-1

6-Chloroindole-2-carboxylic acid ethyl ester

27034-51-1

General method: 6a-d (9.2 mmol) was dissolved in toluene (150 mL) under nitrogen protection, rhodium(II) acetate dimer (203 mg, 0.46 mmol) was added, and the reaction was heated to reflux for 1-2 hours. After completion of the reaction, the solvent was removed by distillation under reduced pressure, and the resulting residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate, 25:1 to 18:1, v/v) to afford the target product ethyl 6-chloroindole-2-carboxylate (7a-d) in 51.7%-58.6% overall yields.

7439-89-6
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Ethyl 3-(4-chloro-2-nitrophenyl)-2-oxopropanoate

540523-98-6
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27034-51-1
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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