116308-35-1

Usage

Uses

Used in Pharmaceutical Industry:
2-(TRIFLUOROMETHYL)NICOTINALDEHYDE is used as a building block for the synthesis of various pharmaceuticals due to its unique reactivity and stability. The trifluoromethyl group enhances the electronegativity of the molecule, which can improve the pharmacological properties of the resulting compounds, such as their potency, selectivity, and metabolic stability.
Used in Agrochemical Industry:
In the agrochemical industry, 2-(TRIFLUOROMETHYL)NICOTINALDEHYDE serves as a key intermediate in the synthesis of agrochemicals with improved performance. The electronegative trifluoromethyl group can enhance the biological activity and selectivity of the final products, making them more effective in controlling pests and diseases in agriculture.
Used in Organic Synthesis:
2-(TRIFLUOROMETHYL)NICOTINALDEHYDE is used as a synthetic intermediate in the production of fluorinated organic compounds. The presence of the trifluoromethyl group allows for the formation of a wide range of fluorinated derivatives with diverse applications in various fields, such as pharmaceuticals, materials science, and specialty chemicals.
Used in Medicinal Chemistry Research:
In medicinal chemistry research, 2-(TRIFLUOROMETHYL)NICOTINALDEHYDE is employed as a valuable tool for the development of new drugs and drug candidates. Its unique reactivity and stability enable the design and synthesis of novel compounds with potential therapeutic applications, contributing to the advancement of drug discovery and development.
Used in Materials Science:
2-(TRIFLUOROMETHYL)NICOTINALDEHYDE also finds applications in materials science, where its electronegative and stable nature can be exploited to develop new materials with improved properties. These materials can be used in various applications, such as sensors, catalysts, and advanced materials for electronic and optoelectronic devices.

InChI:InChI=1/C7H4F3NO/c8-7(9,10)6-5(4-12)2-1-3-11-6/h1-4H

Upstream product

• 131747-57-4 (2-(trifluoromethyl)pyridin-3-yl)methanol 
• 1603-40-3 3-methylpyridin-2-ylamine 
• 3430-17-9 2-bromo-3-picoline 
• 1620-78-6 3-methyl-2-(trifluoromethyl)pyridine 
• 128071-75-0 2-bromopyridine-3-carboxaldehyde 
• 77152-08-0 trifluoromethylcopper(I) 
• 131747-43-8 2-(trifluoromethyl)nicotinic acid 
• 208517-35-5 ethyl 2-(trifluoromethyl)pyridine-3-carboxylate 

Downstream Products

• 116308-45-3 2-(p-Dimethylaminophenyl)ethyl methyl 2,6-dimethyl-4-(2-trifluoromethyl-pyridin-3-yl)-1,4-dihydropyridine-3,5-dicarboxylate 
• 116308-49-7 2-(p-Dibenzylaminophenyl)ethyl methyl 2,6-dimethyl-4-(2-trifluoromethyl-pyridin-3-yl)-1,4-dihydropyridine-3,5-dicarboxylate 
• 116308-53-3 2',6'-Dimethyl-2-trifluoromethyl-1',4'-dihydro-[3,4']bipyridinyl-3',5'-dicarboxylic acid 5'-{2-[4-(4-benzhydryl-piperazin-1-yl)-phenyl]-ethyl} ester 3'-methyl ester 
• 108337-84-4 2-(N-Benzyl-N-methylamino)ethyl Methyl 4-(2-Trifluoromethyl-3-pyridyl)-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate 
• 871583-18-5 methyl 4-(trifluoromethyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxylate 

Relevant academic research and scientific papers

The Hemetsberger-Knittel synthesis of substituted 5-, 6-, and 7-azaindoles

A series of substituted 5-, 6-, and 7-azaindoles were prepared via the Hemetsberger-Knittel reaction. In general, better yields were obtained at higher temperatures and shorter reaction times than required for the formation of the analogous indoles, and in some cases, only decomposition occurred below a minimum temperature. The resulting templates offer up to five sites for subsequent functionalization to allow a wide range of chemical diversity. Georg Thieme Verlag Stuttgart.

Microwave synthesis method of 6-trifluoromethylpyridylaldehyde

The invention relates to a microwave synthesis method of 6-trifluoromethylpyridylaldehyde. According to the method, a reaction is performed in a reaction tank by using a microwave irradiation technique; 1 eq of 6-trifluoromethylpyridinemethanol is added, a solvent is added to dissolve 6-trifluoromethylpyridinemethanol, 0.01-0.1 eq of a catalyst and 1-1.5 eq of an oxidant are added, microwave powerand temperature are set to react after feeding is finished, after the reaction is finished, rotary evaporation and concentration is performed on the reaction solution to obtain a solid product, and finally the solid product is separated and purified to obtain the 6-trifluoromethylpyridylaldehyde. Compared with the prior art, the method provided by the invention has the advantages of short reaction time, mild conditions, few side reactions and high yield, simplifies the production process, reduces the production cost and cycle, is easy to realize the popularization of industrial production, and is especially suitable for large-scale production of an intermediate 6-trifluoromethyl nicotinaldehyde of a colony stimulating factor 1 receptor (CSF-1R) inhibitor.

Preparation method of 2-(trifluoromethyl) pyridine-3-formaldehyde (I)

The invention discloses a preparation method of 2-(trifluoromethyl) pyridine-3-formaldehyde (I), and belongs to the technical field of preparation methods of chemical drug intermediates. Acrolein, ammonium hydroxide and 4,4,4-trifluoro-3-oxobutyraldehyde are used as raw materials, and the 2-(trifluoromethyl) pyridine-3-formaldehyde is prepared through aldimine condensation, cyclization and hydrolysis deprotection. The preparation method of the 2-(trifluoromethyl) pyridine-3-formaldehyde (I) has the advantages that the adopted raw materials are relatively cheap and easy to obtain, the method is simple and convenient to operate, the yield of the product is higher, and the industrialized value is higher.

Heterocyclic chalcone activators of nuclear factor (erythroid-derived 2)-like 2 (Nrf2) with improved in vivo efficacy

Nrf2 activators represent a good drug target for designing agents to treat diseases associated with oxidative stress. Building upon previous work, we designed and prepared a series of heterocyclic chalcone-based Nrf2 activators with reduced lipophilicity

FUNCTIONALIZED HETROARYL ENONES EXHIBITING NRF2 ACTIVATION AND THEIR METHOD OF USE

Pharmaceutical compositions are disclosed, which include functionalized hetroaryl enones and are useful for treating or preventing a disease, disorder or condition associated with an NRF2-regulated pathway and/or which involves oxidative stress.

Copper-mediated perfluoroalkylation of heteroaryl bromides with (phen)CuRF

The attachment of perfluoroalkyl groups onto organic compounds has been a major synthetic goal over the past several decades. Previously, our group reported phenanthroline-ligated perfluoroalkyl copper reagents, (phen)CuR F, which react with aryl iodides and aryl boronates to form the corresponding benzotrifluorides. Herein the perfluoroalkylation of a series of heteroaryl bromides with (phen)CuCF3 and (phen)CuCF 2CF3 is reported. The mild reaction conditions allow the process to tolerate many common functional groups. Perfluoroethylation with (phen)CuCF2CF3 occurs in somewhat higher yields than trifluoromethylation with (phen)CuCF3, creating a method to generate fluoroalkyl heteroarenes that are less accessible from trifluoroacetic acid derivatives.

Trifluoromethylation of aryl and heteroaryl halides with fluoroform-derived CuCF3: Scope, limitations, and mechanistic features

Fluoroform-derived CuCF3 recently discovered in our group exhibits remarkably high reactivity toward aryl and heteroaryl halides, performing best in the absence of extra ligands. A broad variety of iodoarenes undergo smooth trifluoromethylation with the ligandless CuCF3 at 23-50 C to give the corresponding benzotrifluorides in nearly quantitative yield. A number of much less reactive aromatic bromides also have been trifluoromethylated, including pyridine, pyrimidine, pyrazine, and thiazole derivatives as well as aryl bromides bearing electron-withdrawing groups and/or ortho substituents. Only the most electrophilic chloroarenes can be trifluoromethylated, e.g., 2-chloronicotinic acid. Exceptionally high chemoselectivity of the reactions (no side-formation of arenes, biaryls, and C2F5 derivatives) has allowed for the isolation of a large number of trifluoromethylated products in high yield on a gram scale (up to 20 mmol). The CuCF3 reagent is destabilized by CuX coproduced in the reaction, the magnitude of the effect paralleling the Lewis acidity of CuX: CuCl > CuBr > CuI. While SNAr and SRN1 mechanisms are not operational, there is a well-pronounced ortho effect, i.e., the enhanced reactivity of ortho-substituted aryl halides 2-RC6H4X toward CuCF3. Intriguingly, this ortho-effect is observed for R = NO2, COOH, CHO, COOEt, COCH3, OCH3, and even CH3, but not for R = CN. The fluoroform-derived CuCF3 reagent and its reactions with haloarenes provide an unmatched combination of reactivity, selectivity, and low cost.

COMPOSITIONS AND METHODS FOR MODULATING FXR

The present invention relates to compounds of Formula (I), a stereoisomer, enantiomer, a pharmaceutically acceptable salt or an amino acid conjugate thereof; wherein variables are as defined herein; and their pharmaceutical compositions, which are useful as modulators of the activity of Farnesiod X receptors (FXR).