43142-64-9

Usage

Uses

Used in Pharmaceutical Industry:
Ethyl 7-chloroindole-2-carboxylate is used as a building block in the synthesis of pharmaceuticals for its potential role in the development of drug candidates for a variety of therapeutic applications. Its versatile structure allows for further modification and functionalization, making it a valuable component in drug discovery and medicinal chemistry research.
Used in Agrochemical Industry:
Ethyl 7-chloroindole-2-carboxylate is also used as a building block in the synthesis of agrochemicals, contributing to the development of potential chemical compounds for agricultural applications. Its properties and reactivity make it suitable for creating new compounds with desired characteristics for use in crop protection and other related fields.

Upstream product

• 368889-92-3 C₁₁H₁₀ClN₃O₂ 
• 1458040-73-7 (Z)-ethyl α-azido-β-(m-chlorophenyl)acrylate 

Downstream Products

• 53924-05-3 7-chloro-1H-indole 
• 167479-16-5 1-methylindolyl-7-carboxylic acid 
• 95538-48-0 (7-Chloro-3-p-tolylamino-1H-indol-2-yl)-carbamic acid ethyl ester 
• 93704-75-7 3-(2-Amino-phenylamino)-7-chloro-1H-indole-2-carboxylic acid ethyl ester 
• 95306-85-7 Ethyl 1-benzyl-7-chloroindole-2-carboxylate 
• 28899-75-4 7-Chloro-1H-indole-2-carboxylic acid 

Relevant academic research and scientific papers

ZrCl4-promoted facile synthesis of indole derivatives

Zirconium(iv) chloride effectively activates nitrogen (N2) extrusion from aryl azidoacrylates followed by annulation to provide the desired indole products in moderate to good yields. The reaction proceeds at low temperature and in short reaction time and is applicable to a variety of substrates.

Indoles via Knoevenagel-Hemetsberger reaction sequence

A series of substituted indoles have been synthesized by the sequential reaction of aromatic aldehydes with ethyl azidoacetate in the presence of sodium ethoxide to form the corresponding ethyl α-azido-β-arylacrylates (Knoevenagel process) followed by a solvent mediated thermolysis (Hemetsberger process). The isolated yields of the ethyl α-azido-β-arylacrylates were significantly increased when employing the sacrificial electrophile ethyl trifluoroacetate. 1H NMR and coupled 1H-13C NMR analysis of the ethyl α-azido-β-arylacrylates indicate that the condensation is stereospecific - only the Z-isomer could be detected. Solvent mediated thermal treatment of the meta-substituted ethyl α-azido-β- arylacrylates resulted in the formation of both the 5- and 7- substituted indoles - the 5-regioisomer being slightly favored over the 7-regioisomer. Analogous thermal treatment of (2Z, 2Z′)-diethyl 3,3′-(1,3- phenylene)bis(2-azidoacrylate) and (2Z, 2Z′)-diethyl 3,3′-(1,4- phenylene)bis(2-azidoacrylate) exclusively produced pyrroloindoles, diethyl 1,5-dihydropyrrolo[2,3-f]indole-2,6-dicarboxylate and diethyl 1,5-dihydropyrrolo[2,3-f]indole-2,6-dicarboxylate, respectively. Results are also reported which indicate that the α-azido-β-arylacrylates can be used in the subsequent Hemetsberger indolization process without prior purification.