33252-29-8

Usage

Uses

Used in Pharmaceutical Industry:
2-Chloro-6-cyanopyridine is used as a synthetic intermediate for the development of various pharmaceutical compounds. Its unique structure allows it to be a key component in the synthesis of drugs targeting different therapeutic areas, such as anti-inflammatory, anti-cancer, and anti-infective agents.
Used in Chemical Synthesis:
In the field of chemical synthesis, 2-Chloro-6-cyanopyridine serves as a valuable building block for the creation of more complex molecules. Its reactivity and functional groups make it suitable for various chemical reactions, including cross-coupling reactions, which are widely used in the synthesis of organic compounds.
Used in Negishi Coupling Reaction:
2-Chloro-6-cyanopyridine is used as a substrate in a Negishi coupling reaction with an arylzinc halide, catalyzed by Pd-NHC (PEPPSI-Ipr, Catalog No. 668032). This reaction is a powerful method for forming carbon-carbon bonds, which are essential in the synthesis of various organic compounds, including pharmaceuticals, agrochemicals, and advanced materials.

InChI:InChI=1/C6H3ClN2/c7-6-3-1-2-5(4-8)9-6/h1-3H

Upstream product

• 100-70-9 2-Cyanopyridine 
• 2402-95-1 2-chloropyridine-N-oxide 
• 7677-24-9 trimethylsilyl cyanide 
• 143-33-9 sodium cyanide 
• 87512-29-6 2-chloro-6-(methylsulfonyl)pyridine 
• 116570-79-7 N-methoxy-2-chloropyridinium methylsulfate 
• 104727-52-8 ethyl 6-chloropyridine-2-carboximidate 
• 773837-37-9 sodium cyanide 
• 20295-64-1 2-chloropyridine N-oxide hydrochloride 
• 2402-78-0 2,6-dichloropyridine 
• 109-09-1 2-chloropyridine 
• 87512-28-5 2-chloro-6-methylsulfinyl pyridine 
• 77145-64-3 2-chloro-6-methylsulphenylpyridine 

Downstream Products

• 70593-61-2 6-chloropyridine-2-carboxamide 
• 104727-51-7 6-hydroxylhexyl 6-chloropyridine-2-carboximidate 
• 104727-50-6 1,6-hexanediyl di(6-chloropyridine-2-carboximidate) 
• 83621-02-7 6-ethoxy-2-pyridinecarbonitrile 
• 104727-52-8 ethyl 6-chloropyridine-2-carboximidate 
• 99902-95-1 6-(3,4-Dichloro-phenoxy)-pyridine-2-carbonitrile 
• 296776-88-0 4-(6-cyanopyridin-2-yl)benzoic acid methyl ester 
• 205174-21-6 2-cyano-6-(2-methoxyphenyl)pyridine 
• 1012330-68-5 2-cyano-6-(2-(1-(tert-butyldimethylsilyloxy)-3-(4-(phenoxymethyl)phenyl)propyl)oxazol-5-yl)pyridine 
• 1135871-76-9 6-(3-acetyl-phenyl)-pyridine-2-carbonitrile 
• 1159599-84-4 6-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridine-2-carbonitrile 
• 120613-15-2 6-vinylpyridine-2-carbonitrile 
• 1243143-35-2 C₁₅H₁₁F₃N₂O 
• 1243143-36-3 C₁₆H₁₃F₃N₂O₂ 

Relevant academic research and scientific papers

Structure-dependent regioselectivity of a roll-over cyclopalladation occuring at 2,2′-bipyridine-type ligands

In this work, different bipyridine-analogue ligands bearing a dimethylamino group in the meta-position of one of the heterocyclic rings were synthesized and reacted with palladium(II) acetate under identical conditions. Cyclometallated palladium(II) complexes with C,N- or C,N,N’-coordinating chelate ligands are formed which were characterized by elemental analysis, 1H and 13C NMR spectroscopy, and single crystal X-ray diffraction analysis. In the case of the mononuclear, C,N,N’-coordinated complex, which is formed by an attack of the palladium(II) site at of the N-methyl groups, the primarily coordinating acetato ligand is exchanged against a chlorido ligand, which is liberated from the solvent dichloromethane by a nucleophilic substitution reaction. In contrast, cyclometallation occurring at one of the six-membered heterocycles leads to dinuclear acetato-bridged palladium(II) complexes.

A gas-phase study on the cyclometallation of a series of Cp*Ir(III) complexes bearing bidentate pyrimidine ligands

A concerted approach of synthesis and gas phase experiments characterizes the relative cyclometallation barriers of a series of cationic η5-Cp* iridium(III) compounds. The common feature of the investigated compounds is a bidentate N,N’-donor ligand possessing a pyridine site functionalized with a 5-butylpyrimidin-2-yl ring in the 2-position. In addition, the pyridine ring was functionalized with electron-donating or -withdrawing groups. The compounds were characterized by means of NMR and IR spectroscopy and elemental analysis. For the measurements of the relative barriers of the cyclometallation, collision-induced dissociation (CID) experiments were carried out, which revealed a clear dependence of the relative barriers from the nature and the position of the substituents at the pyridine ring could be worked out.

Preparation method of 2, 3-dichloro-6-cyanopyridine

The invention discloses a preparation method of 2, 3-dichloro-6-cyanopyridine, and the method comprises the following steps: by using a metal chloride salt as a catalyst and phosphorus halide as a cocatalyst, carrying out one-step liquid-phase chlorination reaction on raw materials 2-chloro-6-cyanopyridine and chlorine to obtain 2, 3-dichloro-6-cyanopyridine; wherein the metal chloride salt is selected from at least one of WCl6, MoCl5, FeCl3, AlCl3, CuCl2, ZnCl2, RuCl3, SnCl4 and SbCl5, and the cocatalyst is selected from at least one of phosphorus pentachloride, phosphorus trichloride, phosphorus pentabromide and phosphorus tribromide. The method is simple in reaction process, low in production cost and high in target product selectivity and yield, the yield is 90% or above by optimizingreaction conditions, and the method has a good industrial prospect.

Synthesis and structure-activity relationships of amide derivatives of (4,4-difluoro-1,2,3,4-tetrahydro-5H-1-benzazepin-5-ylidene)acetic acid as selective arginine vasopressin V2 receptor agonists

A series of (4,4-difluoro-1,2,3,4-tetrahydro-5H-1-benzazepin-5-ylidene)acetamide derivatives was synthesized, and their structure-activity relationships were examined in order to identify potent and selective arginine vasopressin V2 receptor agonists. Attempts to substitute other chemical groups in place of the 2-pyridilmethyl moiety of 1a led to the discovery that potent V2 binding affinity could be obtained with a wide range of functional groups. This structural tolerance allowed for the manipulation of other attributes, such as selectivity against V1a receptor affinity or avoidance of the undesirable inhibition of cytochrome P450 (CYP), without losing potent affinity for the V2 receptor. Some representative compounds obtained in this study were also found to decrease urine volume in awake rats.

1,3-BENZOTHIAZINONE DERIVATIVES AND USE THEREOF

This invention provides a compound represented by the formula (I) :wherein R1 is a hydrogen atom, a halogen atom, hydroxy, nitro, optionally halogenated alkyl, alkoxy optionally having substituents, acyl or amino optionally having substituents;R2 is pyridyl, furyl, thienyl, pyrrolyl, quinolyl, pyrazinyl, pyrimidinyl, pyridazinyl, indolyl, tetrahydroquinolyl or thiazolyl, each of which may have substituents;n is 1 or 2; or a salt. And this invention provides a safe pharmaceutical comprising the compound of the formula (I) , which has an excellent apoptosis inhibitory effect and MIF binding effect, for preventing and/or treating heart disease, nervous degenerative disease, cerebrovascular disease, central nervous infectious disease, traumatorathy, demyelinating disease, bone and articular disease, kidney disease, liver disease, osteomyelodysplasia, AIDS, cancer, and the like.

Preparation of substituted 2-chloropyridines

A process for the preparation of a substituted 2-chloropyridine derivatives of the formula STR1 in which R1, R2, R3 and R4 represent hydrogen or various other radicals, which comprises reacting a pyridine-1-oxide of the formula STR2 with an aromatic carbonyl chloride in the presence of an inert organic solvent and in the presence of an acid acceptor at a temperature between about -20° C. and 200° C.

Process for the preparation of substituted 2-chloropyridines

A new process has been found for the preparation of substituted 2-chloropyridine derivatives of the formula (I) STR1 wherein R1 to R4 have the meanings as defined in the description. The new process is characterized in that pyridine 1-oxides of the formula II STR2 are reacted with a chlorine-containing phosphoric acid derivative from the series of the chlorophosphoric esters and chlorophosphoramides in the presence of an inert organic solvent and in the presence of an acid acceptor at temperatures between -20° C. and 200° C., and the resulting product is separated further, if appropriate. Compound (I) is known as an intermediate product for medicaments (cf.DE-A 2,812,585) or for insecticidel nitromethylene derivatives (cf. EP-A 163,855).

SOLVENT AND TEMPERATURE DEPENDENT REGIOSELECTIVE REACTIONS BETWEEN 2-CHLORO-6-CYANOPYRIDINE AND ALIPHATIC ALCOHOLS

Reaction of 2-chloro-6-cyanopyridine with aliphatic mono- and di-alcohols or ethylene glycols affords, depending on the reaction conditions, alkoxypyridines or imino ester pyridines or a mixture of both types of compounds.It is suggested that the product distribution is determined by the stability of an imidate anion formed as an intermediate.An improved synthesis of 2-chloro-6-cyanopyridine is also described.

Site-Selectivity in the Cyanation of 3-Substituted Pyridine 1-Oxides with Trimethylsilanecarbonitrile

The cyanation of 3-halo-, 3-methoxy-, and 3-dimethylaminopyridine 1-oxide with trimethylsilanecarbonitrile gave predominantly the corresponding 3-substituted 2-pyridinecarbonitriles.The deoxygenation of nitropyridine 1-oxides to nitropyridines with the same reagent is also described.Keywords - site-selective reaction; trimethylsilanecarbonitrile; pyridine 1-oxide; 2-pyridine-carbonitrile; nitropyridine 1-oxide; deoxygenation; aromatic amine N-oxide; cyanation