53590-46-8

Usage

Uses

Used in Pharmaceutical Research and Development:
Ethyl-4-Chloroindole-2-Carboxylate is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its unique chemical structure and reactivity make it suitable for the development of new drugs with potential therapeutic applications.
Used in Organic Synthesis:
As an ester derivative, Ethyl-4-Chloroindole-2-Carboxylate is utilized in organic synthesis for the preparation of a wide range of chemical compounds. Its versatility allows for the creation of various organic molecules with different functional groups and properties.
Used in Agrochemical Production:
Ethyl-4-Chloroindole-2-Carboxylate is employed in the production of agrochemicals, such as pesticides and herbicides. Its biological activity and chemical properties contribute to the development of effective and targeted agrochemicals for agricultural applications.
Used in Drug Discovery:
Due to its diverse pharmacological effects, Ethyl-4-Chloroindole-2-Carboxylate is used as a starting material in drug discovery. Researchers can modify its structure to explore new drug candidates with potential therapeutic benefits.

Upstream product

• 24621-73-6 4-chloro-1H-indole-2-carboxylic acid 
• 64-17-5 ethanol 
• 83-42-1 6-chloro-2-nitrotoluene 
• 7439-89-6 iron 
• 95-92-1 oxalic acid diethyl ester 
• 617-35-6 2-oxo-propionic acid ethyl ester 
• 108-42-9 3-chloro-aniline 
• 1906-82-7 ethyl acetamidoacetate 
• 64622-16-8 2-bromo-6-chlorobenzaldehyde 
• 2312-23-4 m-chlorophenylhydrazine hydrochloride 
• 36892-19-0 (2-chloro-6-nitro-phenyl)-pyruvic acid 
• 129822-39-5 N-(tert-butoxycarbonyl)-2-amino-6-chlorotoluene 
• 6361-22-4 2-chloro-6-nitrobenzaldehyde 
• 1099-45-2 ethyl (triphenylphosphoranylidene)acetate 

Downstream Products

• 876-72-2 4-chloroindole-3-carboxaldehyde 

Relevant academic research and scientific papers

A facile synthesis of 2-substituted indoles from (2-aminobenzyl)triphenylphosphonium salts

A variety of 2-substituted 1-acylindoles were obtained in yields ranging from 40 to 94% by intramolecular Wittig reaction employing (2-aminobenzyl)triphenylphosphonium derivatives and acid anhydride in the presence of triethylamine. The reaction of (2-ami

Synthesis method for preparing 2-substituted indole derivative

The invention relates to a synthesis method for preparing a 2-substituted indole derivative. The method includes the following steps: mixing aromatic amine compounds (I), ketone compounds (II) and a drying agent in an organic solvent; adding a palladium catalyst; and reacting in an aerobic weak acid environment to prepare the indole compounds (III). (I), (II) and (III) are as shown in the specification, wherein R1 is selected from hydrogen, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkanoyl, C2-C6 alkenyl, C2-C6 alkynyl, halogen, hydroxyl, substituted or unsubstituted amino, substituted or unsubstituted phenyl, pyridyl and heterocyclic aryl; (I) can be pyridylamine, pyrimidylamine, pyridazinam or pyrazinamide which may further be substituted or unsubstituted; and the substituents are selected fromone or more C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkanoyl, C2-C6 alkenyl, C2-C6 alkynyl, halogen, hydroxyl, amino; and R2 is selected from C1-C6 alkyl, formate groups or C1-C6 alkylamide groups.

Carboxylic Acid-Promoted Single-Step Indole Construction from Simple Anilines and Ketones via Aerobic Cross-Dehydrogenative Coupling

The cross-dehydrogenative coupling (CDC) reaction is an efficient strategy for indole synthesis. However, most CDC methods require special substrates, and the presence of inherent groups limits the versatility for further transformation. A carboxylic acid-promoted aerobic catalytic system is developed herein for a single-step synthesis of indoles from simple anilines and ketones. This versatile system is featured by the broad substrate scope and the use of ambient oxygen as an oxidant and is convenient and economical for both laboratory and industry applications. The existence of the labile hydrogen at C-3 and the highly transformable carbonyl at C-2 makes the indoles versatile building blocks for organic synthesis in different contexts. Computational studies based on the density functional theory (DFT) suggest that the rate-determining step is carboxylic acid-assisted condensation of the substrates, rather than the functionalization of aryl C-H. Accordingly, a pathway via imine intermediates is deemed to be the preferred mechanism. In contrast to the general deduction, the in situ formed imine, instead of its enamine isomer, is believed to be involved in the first ligand exchange and later carbopalladation of the α-Me, which shed new light on this indolization mechanism.

Cu nanoparticles immobilized on montmorillonite by biquaternary ammonium salts: a highly active and stable heterogeneous catalyst for cascade sequence to indole-2-carboxylic esters

Copper nanoparticles immobilized on montmorillonite (MMT) by biquaternary ammonium salts (N1,N6-dibenzyl-N1,N1,N6,N6-tetramethylheptane-1,6-diaminium bromide, Q) were prepared by cation-exchange and impregnation-reduction and designated Cu-Q-MMT. The material was extensively characterized by various characterization techniques such as FTIR, XRD, XPS, SEM, TEM, and N2 adsorption-desorption. The Cu-Q-MMT could be used as a highly active heterogeneous catalyst for cascade sequence to indole-2-carboxylic esters from ortho-bromobenzaldehydes with ethyl acetamidoacetate. Even for inactive chlorobenzaldehydes, a good yield could be obtained. In addition, the catalyst can be reused six times without any significant loss of activity. The high activity and stability of the Cu-Q-MMT catalyst is mainly attributed to the excellent synergistic effects of biquaternary ammonium salts, Cu nanoparticles and the nanospace structure of MMT.

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.

Efficient synthesis of 2-ethoxycarbonyl indoles

An efficient one-pot procedure for the synthesis of 2-ethoxycarbonyl indoles from commercially available materials has been developed. The one-step procedure involves in situ formation of the hydrazones from phenylhydrazine hydrochloride and ethyl pyruvate in the presence of bismuth nitrate followed by Fischer cyclization in polyphosphoric acid and ethanol. This method is efficient and simple.

Dioxomolybdenum(VI)-catalyzed reductive cyclization of nitroaromatics. Synthesis of carbazoles and indoles

Reductive cyclization of nitrobiphenyls and nitrostyrenes to carbazoles and indoles, respectively, is carried out by triphenylphosphine under mild conditions catalyzed by a dichlorodioxomolybdenum(VI) complex. A one-pot procedure for the synthesis of regioselectively functionalized indoles has been developed from commercially available onitrobenzaldehydes and phosphoranes.

PYRAZINO(AZA)INDOLE DERIVATIVES

Chemical compounds of formula (I): and pharmaceutically acceptable salts and addition compounds and prodrugs thereof are useful in therapy, particularly for the treatment of disorders of the central nervous system; damage to the central nervous system; ca

Monocyte chemoattractant protein-1 inhibitor compounds

The invention concerns the use of a compound of the formula (I) in which Z, X, T, A, R1, R2, p and q have any of the meanings defined herein, and their pharmaceutically acceptable salts or in vivo hydrolysable esters, in the treatment of a disease or condition mediated by monocyte chemoattractant protein-1 (MCP-1). Certain of the components of formula (I) are novel and are provided, together with pharmaceutical compositions thereof, as further features of the invention.

Synthesis of indole-2-carboxylic acid esters

The title compounds were prepared via lateral lithiation of N-Boc protected toluidines with sec-BuLi, quench with diethyl oxalate, followed by dehydration in TFA/CH2Cl2.