2613-38-9

Usage

InChI:InChI=1/C13H8F3NO2/c14-13(15,16)10-6-7-11(12(8-10)17(18)19)9-4-2-1-3-5-9/h1-8H

Upstream product

• 400-98-6 4-trifluoromethyl-2-nitroaniline 
• 71-43-2 benzene 
• 320-94-5 2-nitro-4-trifluoromethylbenzoic acid 
• 349-03-1 1-bromo-4-trifluoromethyl-2-nitrobenzene 
• 98-80-6 phenylboronic acid 
• 108-86-1 bromobenzene 
• 367-86-2 1-fluoro-2-nitro-4-trifluoromethyl-benzene 
• 121-17-5 2-chloro-3-nitro-5-trifluoromethylbenzene 

Relevant academic research and scientific papers

PHENYL-SULFAMOYL.BENZOYC ACIDS AS ERAP1 MODULATORS

The present invention relates to a compound of formula (I), or a pharmaceutically acceptable salt or hydrate thereof, wherein: the group X-Y is -NHSO2- or -SO2NH-; Z is a monocyclic aryl or heteroaryl group, each of which is optionally substituted by one ormore substituents selected from alkyl, cycloalkyl, halo, alkoxy, CN, haloalkyl and OH; R1 is H or alkyl; R2 is selected from COOH and a tetrazolyl group; R3 is selected from H, C land alkyl; R4 is selected from H and halo; R5 is selected from H, alkyl, haloalkyl, SO2-alkyl,Cl, alkoxy, OH, CN, hydroxyalkyl, alkylthio, heteroaryl, cycloalkyl, heterocycloalkyl andhaloalkoxy; R6 is H; R7 is selected from H, CN, haloalkyl, halo, SO2-alkyl,SO2NR12R13, heteroaryl, CONR10R11 and alkyl, wherein said heteroaryl group is optionallysubstituted by one or more substituents selected from alkyl, halo, alkoxy, CN, haloalkyl and OH; R8 is selected from H, alkyl, haloalkyl and halo; and R9 is H, alkyl or halo; R10 and R11 are each independently H or alkyl; and R12 and R13 are each independently H or alkyl. Further aspects of the invention relate to such compounds for use in the field of immuno- oncology and related applications. Another aspect of the invention relates to compounds of formulae (la) and (lb).

N,N,N′,N′-tetra(diphenylphosphinomethyl)pyridine-2,6-diamine/palladium catalyzed Suzuki-Miyaura coupling of aryl and heteroaryl halides

An easily synthesized tetraphosphine N,N,N′,N′-tetra(diphenylphosphinomethyl)-pyridine-2,6-diamine (TPPDA) in combination with PdCl2 was proved to be a highly efficient catalyst for Suzuki-Miyaura cross-coupling. This system could catalyze a variety of aryl halide substrates with a wide range of functional groups as well as heteroaryl halides. A high turnover number (TON) up to 3,350,000 was reached for 3-bromochlorobenzene.

Silver-catalyzed arylation of (hetero)arenes by oxidative decarboxylation of aromatic carboxylic acids

A long-standing challenge in Minisci reactions is achieving the arylation of heteroarenes by oxidative decarboxylation of aromatic carboxylic acids. To address this challenge, the silver-catalyzed intermolecular Minisci reaction of aromatic carboxylic acids was developed. With an inexpensive silver salt as a catalyst, this new reaction enables a variety of aromatic carboxylic acids to undergo decarboxylative coupling with electron-deficient arenes or heteroarenes regardless of the position of the substituents on the aromatic carboxylic acid, thus eliminating the need for ortho-substituted aromatic carboxylic acids, which were a limitation of previously reported methods.

Transition-metal-free synthesis of phenanthridinones from biaryl-2-oxamic acid under radical conditions

Na2S2O8-promoted decarboxylative cyclization of biaryl-2-oxamic acid for phenanthridinones has been developed. This work illustrates the first example of intramolecular decarboxylative amidation of unactivated arene under transition-metal-free conditions. Additionally, this approach provides an efficient and economical method to access biologically interesting phenanthridinones, an important structure motif in many natural products. (Chemical Equation Presented).

An easily prepared tetraphosphine and its use in the palladium-catalyzed Suzuki-Miyaura coupling of aryl chlorides

An air-stable tetraphosphine N,N,N′,N′- tetra(diphenylphosphinomethyl)-benzene-1,3-diamine (L3) was easily prepared in two steps from triphenylphosphine, which in combination with [Pd(η3-C3H5)Cl]2 affords an efficient catalyst for Suzuki-Miyaura coupling of activated chloroarenes. Even at high temperature of 130 C, this catalyst exhibits good stability and longevity, and could allow a high turnover number of 680,000 to be reached. Graphical Abstract: [Figure not available: see fulltext.].

Triphenylphosphine-mediated reductive cyclization of 2-nitrobiphenyls: A practical and convenient synthesis of carbazoles

The synthesis of a series of substituted carbazoles from the corresponding 2-nitrobiphenyl derivatives using a novel modification of the Cadogan reaction is described. Cyclization of the 2-nitrobiphenyls was achieved via reductive deoxygenation of the nitro groups using a slight excess of triphenylphosphine in a suitable solvent. We have observed a temperature dependence on the extent of conversion under these conditions, with higher boiling solvents affording higher yields across a range of substrates. The new reaction conditions are very straightforward and convenient to execute, tolerate a broad range of functional groups, and yield carbazole products in the absence of unwanted side products.

Palladium catalysed Suzuki reactions of fluoroarenes

A novel palladium catalysed cleavage of C-F bonds in a series of Suzuki reactions of aryl fluorides is described together with a discussion of the mechanistic implications.

Palladium catalysed cross-coupling of aryl chlorides with arylboronic acids in the presence of a new tetraphosphine ligand

Cis,cis,cis-1,2,3,4-tetrakis(diphenylphosphinomethyl)cyclo pentane/[PdCl(C3H5)]2 system catalyses the cross-coupling of aryl chlorides with arylboronic acids with high ratios substrate/catalyst. A turnover number of 6800000 has been obtained for the addition of the activated 2-chloro-5-(trifluoromethyl)nitrobenzene to benzeneboronic acid in the presence of this catalyst.