348-32-3

Usage

Uses

Used in Pharmaceutical Research:
Ethyl-4-Fluoroindole-2-Carboxylate is used as a precursor in the synthesis of various drugs and biologically active molecules. Its unique structure and functional groups make it a valuable building block for creating new pharmaceutical agents with potential therapeutic applications.
Used in Medicinal Chemistry:
Ethyl-4-Fluoroindole-2-Carboxylate is employed as a lead compound in drug discovery and development. Its pharmacological properties and biological activities are being investigated to identify potential therapeutic targets and develop novel treatments for various diseases.
Used in Agrochemicals:
In the agrochemical industry, Ethyl-4-Fluoroindole-2-Carboxylate is used as a starting material for the synthesis of agrochemicals, such as pesticides and herbicides. Its unique chemical properties allow for the development of new compounds with improved efficacy and selectivity.
Used in Material Science:
Ethyl-4-Fluoroindole-2-Carboxylate is utilized in the field of material science for the development of new materials with specific properties. Its chemical structure and functional groups can be exploited to create materials with applications in various industries, such as electronics, coatings, and adhesives.

InChI:InChI=1/C11H10FNO2/c1-2-15-11(14)10-6-7-8(12)4-3-5-9(7)13-10/h3-6,13H,2H2,1H3

Upstream product

• 404-69-3 (E)-ethyl 2-(2-(3-fluorophenyl)hydrazin-1-ylidene)propanoate 
• 75-03-6 ethyl iodide 
• 796069-23-3 4-fluoroindole-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester 
• 617-35-6 2-oxo-propionic acid ethyl ester 
• 372-19-0 meta-fluoroaniline 
• 446-52-6 2-Fluorobenzaldehyde 
• 1309834-27-2 C₁₁H₁₀FN₃O₂ 

Downstream Products

• 220677-36-1 Ethyl N-(3,4-dichlorobenzyl)-4-fluoroindole-2-carboxylate 

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.

Indol-2-yl ethanones as novel indoleamine 2,3-dioxygenase (IDO) inhibitors

Indoleamine 2,3-dioxygenase (IDO) is a heme dioxygenase which has been shown to be involved in the pathological immune escape of diseases such as cancer. The synthesis and structure-activity relationships (SAR) of a novel series of IDO inhibitors based on the indol-2-yl ethanone scaffold is described. In vitro and in vivo biological activities have been evaluated, leading to compounds with IC50 values in the micromolar range in both tests. Introduction of small substituents in the 5- and 6-positions of the indole ring, indole N-methylation and variations of the aromatic side chain are all well tolerated. An iron coordinating group on the linker is a prerequisite for biological activity, thus corroborating the virtual screening results.

Heterocyclyl-substituted dihydroquinazolines and their use as antiviral agents

The invention relates to heterocyclyl-substituted dihydroquinazolines of formula (I), to processes for their preparation, to medicaments containing them, and to methods for the treatment and/or prophylaxis of diseases, in particular, for use as anti-viral agents, in particular, against cytomegaloviruses.

HETEROCYCLYL-SUBSTITUTED DIHYDROQUINAZOLINES AND USE THEREOF AS AN ANTIVIRAL AGENT

The invention relates to heterocyclyl-substituted dihydroquinazolines of formula (I), methods for the production and use thereof for the production of medicaments for the treatment and/or prophylaxis of diseases, in particular, for use as anti-viral agents, in particular, against cytomegaloviruses.

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.