43142-25-2

Usage

Chemical class

Indole

Functional groups

Carboxylic acid, methoxy, ethyl ester

Molecular weight

219.24 g/mol

Appearance

Solid

Solubility

Soluble in organic solvents, insoluble in water

Use

Intermediate in organic synthesis for pharmaceuticals and agrochemicals

Biological activities

Being studied for pharmacological properties

Chemical structure

An indole ring with a carboxylic acid group and a methoxy substituent at the 4-position, with an ethyl ester group attached to the carboxylic acid.

Upstream product

• 103260-65-7 4-methoxy-1H-indole-2-carboxylic acid 
• 64-17-5 ethanol 
• 112238-07-0 ethyl 2-(2-methoxyphenyl)-2H-azirine-3-carboxylate 
• 301155-92-0 3-(2-Methoxy-6-nitro-phenyl)-2-oxo-propionic acid ethyl ester 
• 185212-06-0 α-Azido-2-methoxy-zimtsaeure-aethylester 
• 24513-01-7 ethyl (Z)-2-azido-3-(2-methoxyphenyl)acrylate 
• 617-35-6 2-oxo-propionic acid ethyl ester 
• 536-90-3 m-Anisidine 

Downstream Products

• 213682-04-3 4-methoxy-1H-indole-2-carbaldehyde 

Relevant academic research and scientific papers

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.

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.

Tripeptidylpeptidase inhibitors

A compound of formula wherein the substituents are defined as in the specification and salts or hydrates thereof is disclosed as well as a method of treating disorders associated with the inactivation or excessive degradation of cholecystokinin.

Unexpected formation of quinolone derivatives in Reissert indole synthesis

The Reissert indole synthesis was found to unexpectedly give 3-hydroxy-1,2,3,4-tetrahydro-2-quinolone derivative 4, sometimes in a high ratio with the expected ethyl indole-2-carboxylate derivatives 3 in a low ratio, depending on the conditions of the catalytic reduction of the intermediate 2-nitrophenylpyruvate 2. This reactivity is characteristic in the preparation of 7-substituted indoles.

Novel Cyclization of Vinyl Nitrene into 1-Azaphenalene

Thermal reaction of 2H-azirines, bearing a methoxy or methylthio group at the neighboring position to azirine ring, was studied.In thermolysis of ethyl 2-(2-methoxynaphth-1-yl)-2H-azirine-3-carboxylate, attack of the vinyl nitrene at the peri position to form a 1-azaphenalene ring was observed.In thermal reaction of its thio analogue, 1-azaphenalene was also formed, but a naphthotiazine formed by the attack of vinyl nitrene at the sulfur atom was the major product.Mechanisms and differences of the reactions depending on O and S are discussed.