348-37-8

Usage

Uses

Used in Pharmaceutical Industry:
Ethyl 6-fluoroindole-2-carboxylate is used as an intermediate in the synthesis of pharmaceuticals for its potential to target central nervous system disorders, cancer, and infectious diseases. Its unique structure allows for the development of drugs with specific therapeutic effects.
Used in Agrochemical Industry:
In the agrochemical sector, Ethyl 6-fluoroindole-2-carboxylate is utilized as an intermediate in the synthesis of agrochemicals, contributing to the development of effective and targeted pest control agents.
Used in Organic Materials Industry:
Ethyl 6-fluoroindole-2-carboxylate also serves as an intermediate in the synthesis of organic materials, where its structural features can be leveraged to create novel materials with specific properties for various applications.
Used in Medicinal Chemistry Research:
Ethyl 6-fluoroindole-2-carboxylate is used as a valuable building block in medicinal chemistry research, enabling the exploration of new drug candidates and the enhancement of existing drug therapies through structural modifications.

Upstream product

• 404-69-3 (E)-ethyl 2-(2-(3-fluorophenyl)hydrazin-1-ylidene)propanoate 
• 346-43-0 ethyl (4-fluoro-2-nitrophenyl)pyruvate 
• 59142-68-6 2-bromo-4-fluorobenzaldehyde 
• 623-33-6 glycine ethyl ester hydrochloride 
• 617-35-6 2-oxo-propionic acid ethyl ester 
• 372-19-0 meta-fluoroaniline 
• 446-10-6 2-nitro-4-fluorotoluene 
• 3093-97-8 6-fluoro-1H-indole-2-carboxylic acid 
• 64-17-5 ethanol 
• 127-17-3 2-oxo-propionic acid 
• 658-27-5 m-fluorophenylhydrazine 
• 459-57-4 4-fluorobenzaldehyde 
• 911301-34-3 ethyl 2-azido-3-(4-fluorophenyl)acrylate 

Downstream Products

• 3093-97-8 6-fluoro-1H-indole-2-carboxylic acid 
• 399-51-9 6-fluoro-1H-indole 
• 840474-96-6 6-fluoro-1-(phenylsulfonyl)-1H-indole 
• 1394431-16-3 lithium 6-fluoro-1-(phenylsulfonyl)-1H-indole-2-sulfinate 
• 1394431-17-4 6-fluoro-1-(phenylsulfonyl)-1H-indole-2-sulfonyl chloride 
• 1394431-18-5 N-(biphenyl-4-ylmethyl)-6-fluoro-1-(phenylsulfonyl)-1H-indole-2-sulfonamide 
• 1394431-19-6 N-(biphenyl-4-ylmethyl)-6-fluoro-1H-indole-2-sulfonamide 

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.

INDOLE DERIVATIVE, PREPARATION METHOD THEREOF, AND USE THEREOF IN PHARMACEUTICAL DRUG

An indole derivative as expressed by Formula (I), a preparation method thereof, a pharmaceutical salt, and use thereof as a therapeutic agent, especially as a FGFR inhibitor. Each substituent in Formula (I) has identical definition as specified in the specification.

NOVEL COMPOUND, PROCESS FOR THE PREPARATION THEREOF AND PHARMACEUTICAL COMPOSITION COMPRISING THE SAME

The present invention relates to a novel compound controlling the phosphorylation of PPARandgamma; by CDK5, a process for the preparation thereof, and a pharmaceutical composition comprising the same. The novel compound of the present invention combines t

Development of indole sulfonamides as cannabinoid receptor negative allosteric modulators

Existing CB1 negative allosteric modulators (NAMs) fall into a limited range of structural classes. In spite of the theoretical potential of CB1 NAMs, published in vivo studies have generally not been able to demonstrate the expected therapeutically-relevant CB1-mediated effects. Thus, a greater range of molecular tools are required to allow definitive elucidation of the effects of CB1 allosteric modulation. In this study, we show a novel series of indole sulfonamides. Compounds 5e and 6c (ABD1075) had potencies of 4 and 3?nM respectively, and showed good oral exposure and CNS penetration, making them highly versatile tools for investigating the therapeutic potential of allosteric modulation of the cannabinoid system.

Ligand-free copper-catalyzed one-pot synthesis of indole-2-carboxylic esters

A simple, efficient, and facile synthetic route for the preparation of indole-2-carboxylic esters was described. The cascade reactions of 2-bromobenzaldehyde and glycine ester hydrochloride were promoted by Cu 2O and a base to provide the corresponding products in good yields. Commercially available, inexpensive substrates and reagents were employed under mild reaction conditions in this one-pot operation, which is complementary to existing methods for access to 2-substituted indoles. A simple, efficient, and facile synthetic route to indole-2-carboxylic esters through copper-catalyzed one-pot cascade reactions of commercially available, inexpensive 2-bromobenzaldehyde and glycine ester hydrochloride without the use of any external ligand under mild conditions is reported. Copyright

Ligand-Free Copper-Catalyzed One-Pot Synthesis of Indole-2-carboxylic Esters

A simple, efficient, and facile synthetic route for the preparation of indole-2-carboxylic esters was described. The cascade reactions of 2-bromobenzaldehyde and glycine ester hydrochloride were promoted by Cu2O and a base to provide the corresponding products in good yields. Commercially available, inexpensive substrates and reagents were employed under mild reaction conditions in this one-pot operation, which is complementary to existing methods for access to 2-substituted indoles.

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.

Synthesis and anti-tumor activity of 2-amino-3-cyano-6-(1H-indol-3-yl)-4- phenylpyridine derivatives in vitro

A series of novel 2-amino-3-cyano-6-(1H-indol-3-yl)-4-phenylpyridine derivatives were synthesized and their cytotoxic activity against A549, H460, HT-29 and SMMC-7721 cell lines was evaluated in vitro. Among them, ten compounds (10, 11, 14, 16, 17, 26, 27, 29, 30 and 31) displayed excellent anti-tumor activity against different cell lines. The most promising compound 27 showed strong anti-tumor activity against A549, H460, HT-29 and SMMC-7721 cell lines with IC50 values of 22, 0.23, 0.65 and 0.77 nM, which were 2.6-, 83-, 1.1 × 103- and 2.0 × 103- fold more active than MX-58151 (IC50 values of 0.058, 0.019, 0.70 and 1.53 μM), respectively.

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.