58254-76-5

Usage

Synthesis Reference(s)

Tetrahedron Letters, 32, p. 2273, 1991 DOI: 10.1016/S0040-4039(00)79700-0

InChI:InChI=1/C11H8ClN/c12-10-6-7-11(13-8-10)9-4-2-1-3-5-9/h1-8H

Upstream product

• 16110-09-1 2,5 dichloropyridine 
• 98-80-6 phenylboronic acid 
• 40473-01-6 2-Bromo-5-chloro-pyridine 
• 108-86-1 bromobenzene 
• 98-86-2 acetophenone 
• 201230-82-2 carbon monoxide 
• 652148-91-9 (5-chloropyridin-2-yl)boronic acid 
• 100-59-4 phenylmagnesium chloride 
• 626-60-8 3-Chloropyridine 
• 13471-35-7 dimethyl phenylboronate 
• 603-33-8 triphenylbismuthane 
• 591-50-4 iodobenzene 
• 4214-79-3 5-chloro-1,2-dihydropyridin-2-one 
• 5123-13-7 5,5-dimethyl-2-phenyl-1,3,2-dioxaborinane 

Downstream Products

• 480390-54-3 ethyl 4-(3-chloro-6-phenyl-2-pyridyl)benzoate 
• 1421006-68-9 (E)-5-chloro-2-(2-(2-methylstyryl)phenyl)pyridine 
• 1414972-04-5 2-phenyl-5-(prop-1-en-2-yl)pyridine 
• 66562-61-6 3-ethyl-6-phenylpyridine 
• 1584673-26-6 5-chloro-2-(2-(phenylthio)phenyl)pyridine 
• 1519065-39-4 benzyl 2-(5-chloropyridin-2-yl)phenylcarbamate 
• 1574299-47-0 C₁₈H₁₄ClNO 

Relevant academic research and scientific papers

Discovery of 9,10-dihydrophenanthrene derivatives as SARS-CoV-2 3CLpro inhibitors for treating COVID-19

The epidemic coronavirus disease 2019 (COVID-19) caused by severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) has now spread worldwide and efficacious therapeutics are urgently needed. 3-Chymotrypsin-like cysteine protease (3CLpro) is an indispensable protein in viral replication and represents an attractive drug target for fighting COVID-19. Herein, we report the discovery of 9,10-dihydrophenanthrene derivatives as non-peptidomimetic and non-covalent inhibitors of the SARS-CoV-2 3CLpro. The structure-activity relationships of 9,10-dihydrophenanthrenes as SARS-CoV-2 3CLpro inhibitors have carefully been investigated and discussed in this study. Among all tested 9,10-dihydrophenanthrene derivatives, C1 and C2 display the most potent SARS-CoV-2 3CLpro inhibition activity, with IC50 values of 1.55 ± 0.21 μM and 1.81 ± 0.17 μM, respectively. Further enzyme kinetics assays show that these two compounds dose-dependently inhibit SARS-CoV-2 3CLpro via a mixed-inhibition manner. Molecular docking simulations reveal the binding modes of C1 in the dimer interface and substrate-binding pocket of the target. In addition, C1 shows outstanding metabolic stability in the gastrointestinal tract, human plasma, and human liver microsome, suggesting that this agent has the potential to be developed as an orally administrated SARS-CoV-2 3CLpro inhibitor.

Compound, light extraction material and organic electroluminescent device

The present application provides a compound of general formula (I), and the compound can be used in light extraction materials. Pyridine and connected aromatic groups in the parent nucleus structure of the compound have good planarity, and the compound ca

Compound, electron transport material and organic electroluminescent device

The present application provides a compound of general formula (I), which can be used in an electron transport material. The compound is high in bond energy among atoms, good in thermal stability, beneficial to solid-state accumulation among molecules, hi

Ruthenium-Catalyzed Reductive Cleavage of Unstrained Aryl-Aryl Bonds: Reaction Development and Mechanistic Study

Cleavage of carbon-carbon bonds has been found in some important industrial processes, for example, petroleum cracking, and has inspired development of numerous synthetic methods. However, nonpolar unstrained C(aryl)-C(aryl) bonds remain one of the toughest bonds to be activated. As a detailed study of a fundamental reaction mode, here a full story is described about our development of a Ru-catalyzed reductive cleavage of unstrained C(aryl)-C(aryl) bonds. A wide range of biaryl compounds that contain directing groups (DGs) at 2,2′ positions can serve as effective substrates. Various heterocycles, such as pyridine, quinoline, pyrimidine, and pyrazole, can be employed as DGs. Besides hydrogen gas, other reagents, such as Hantzsch ester, silanes, and alcohols, can be employed as terminal reductants. The reaction is pH neutral and free of oxidants; thus a number of functional groups are tolerated. Notably, a one-pot C-C activation/C-C coupling has been realized. Computational and experimental mechanistic studies indicate that the reaction involves a ruthenium(II) monohydride-mediated C(aryl)-C(aryl) activation and the resting state of the catalyst is a η4-coordinated ruthenium(II) dichloride complex, which could inspire development of other transformations based on this reaction mode.

Transition-Metal-Free Desulfinative Cross-Coupling of Heteroaryl Sulfinates with Grignard Reagents

A mild cross-coupling reaction of heteroaryl sulfinates with Grignard reagents has been developed under transition-metal-free conditions. This study provides an example of the SO22- as a leaving group in an aromatic system and an effective methodology for the construction of C-C bond.

Cobalt-Catalyzed Cross-Coupling Reactions of Arylboronic Esters and Aryl Halides

An efficient cobalt catalyst system for the Suzuki-Miyaura cross-coupling reaction of arylboronic esters and aryl halides has been identified. In the presence of cobalt(II)/terpyridine catalyst and potassium methoxide, a diverse array of (hetero)biaryls have been prepared in moderate to excellent yields.

Preparation method for biaryl compound

The invention provides a preparation method for a biaryl compound. The preparation method comprises the step of performing cross coupling reaction on a substrate A and an organic zinc reagent B under a catalytic effect of a catalyst, thereby acquiring the biaryl compound, wherein a chemical structure of the substrate A is shown in the description; the organic zinc reagent B has the chemical structure shown in the description; and the catalyst is one or more of nickel salt, copper salt and cobalt salt. Compared with the other noble metal catalysts, such as, metal palladium catalyst, the catalyst adopting nickel salt, copper salt or cobalt salt is low in cost, so that the reaction cost of the biaryl compound is greatly reduced. Meanwhile, the aryl sulphonate or aryl halide shown as the substrate A has an excellent electrophilic property, is an electrophilic reagent with an excellent property and has the advantages of easiness in preparation, low cost, high activity and high stability. The substrate A and the organic zinc reagent B have cross coupling reaction under the effect of nickel salt, copper salt or cobalt salt so as to generate the biaryl compound and the reaction yield is higher.

Synthesis of zwitterionic palladium complexes and their application as catalysts in cross-coupling reactions of aryl, heteroaryl and benzyl bromides with organoboron reagents in neat water

N-(3-Chloro-2-quinoxalinyl)-N′-arylimidazolium salts (aryl = 2,6-diisopropylphenyl [HL1Cl]Cl, aryl = mesityl [HL2Cl]Cl) have been synthesized by treating 2,3-dichloroquinoxaline with the corresponding N′-arylimidazole in neat water. Facile reactions of these imidazolium salts with Pd(PPh3)4 and Pd2(dba)3/PPh3 (dba = dibenzyledene acetone) at 50 °C have afforded zwitterionic palladium(ii) complexes [Pd(HL1)(PPh3)Cl2] (I) and [Pd(HL2)(PPh3)Cl2] (II) in excellent yields. I and II have been tested for their ability to catalyze Suzuki-Miyaura cross coupling (SMC) reactions in neat water/K2CO3 and are found to be highly active for carrying out these reactions between aryl bromides and organoboron reagents. Furthermore, the scope of the catalyst I was also examined by employing (hetero)aryl bromides, hydrophilic aryl bromides, benzyl bromides and various organoboron reagents. More than 80 aryl/benzyl bromide-arylboronic acid combinations were screened in neat water/K2CO3 and it was found that I was a versatile catalyst, which produced biaryls/diarylmethanes in excellent yields. A TON of 82 000 was achieved by using I. Studies on the mechanism have also been carried out to investigate the involvement of carbene complexes in the catalytic path. Poison tests and a two-phase test were also conducted and the results are reported.

Ru-Catalyzed Regioselective Direct Hydroxymethylation of (Hetero)Arenes via C-H Activation

An efficient and direct ruthenium-catalyzed regioselective hydroxymethylation of (hetero)arenes via C-H activation with paraformaldehyde as a hydroxymethylating reagent is described. The corresponding products can be obtained in good to excellent yield. A number of aryl aldehydes can also be used in place of paraformaldehyde giving the desired alcohol products with similarly good results.

Pd(II)-catalyzed monoarylation of 2-phenylpyridine N-oxide with iodobenzene in water

A Pd(II)-catalyzed activation and arylation of C(sp2)–H bond directed by pyridine N-oxide in water is achieved with high regioselectivity to form monoarylated products in yields up to 91%. The wide substrate scope highlights the flexibility of the catalyst. The reaction mechanism was proposed and the application of this method was taken as an example by the synthesis of COX-2 inhibitor analog.