5958-01-0

Basic information

• Product Name: 3-(2-METHOXYPHENYL)PYRIDINE
• Synonyms: 3-(2-METHOXYPHENYL)PYRIDINE;AKOS BAR-0418
• CAS NO: 5958-01-0
• Molecular Formula: C₁₂H₁₁NO
• Molecular Weight: 185.22
• Mol File: 5958-01-0.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-(2-METHOXYPHENYL)PYRIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(2-METHOXYPHENYL)PYRIDINE(5958-01-0)
• EPA Substance Registry System: 3-(2-METHOXYPHENYL)PYRIDINE(5958-01-0)

Safety Data

• Hazardous Substances Data: 5958-01-0(Hazardous Substances Data)

Upstream product

• 626-60-8 3-Chloropyridine 
• 100-66-3 methoxybenzene 
• 766-51-8 2-Chloroanisole 
• 1692-25-7 3-pyridylboronic acid 
• 578-57-4 2-bromoanisole 
• 5720-06-9 2-Methoxyphenylboronic acid 
• 110-86-1 pyridine 
• 6971-45-5 2-methoxyphenylhydrazine hydrochloride 
• 626-55-1 3-Bromopyridine 
• 59-67-6 nicotinic acid 
• 3468-53-9 phenyl nicotinate 
• 1439071-05-2 C₁₄H₁₆N₂O₃S 
• 89878-14-8 3-Diethylboranylpyridine 
• 2510-23-8 3-Ethynylpyridine 

Downstream Products

• 54168-07-9 3-(2-hydroxyphenyl)pyridine 
• 851595-35-2 2-chloro-5-(2-methoxy-phenyl)-pyridine 
• 19737-63-4 3-(2-methoxyphenyl)-piperidine 
• 851595-47-6 2,3-dichloro-5-(2-methoxy-phenyl)-pyridine 

Relevant articles and documents

Decarbonylative Pd-Catalyzed Suzuki Cross-Coupling for the Synthesis of Structurally Diverse Heterobiaryls

Heteroaromatic biaryls are core scaffolds found in a plethora of pharmaceuticals; however, their direct synthesis by the Suzuki cross-coupling is limited to heteroaromatic halide starting materials. Here, we report a direct synthesis of diverse nitrogen-containing heteroaromatic biaryls by Pd-catalyzed decarbonylative Suzuki cross-coupling of widely available heterocyclic carboxylic acids with arylboronic acids. The practical and modular nature of this cross-coupling enabled the straightforward preparation of >45 heterobiaryl products using pyridines, pyrimidines, pyrazines, and quinolines in excellent yields. We anticipate that the modular nature of this protocol will find broad application in medicinal chemistry and drug discovery research.

An active catalytic system for Suzuki-Miyaura cross-coupling reactions using low levels of palladium loading

An easily available Pd(OAc)2/(2-(anthracen-9-yl)-1H-inden-3-yl) dicyclohexylphosphine/toluene/iPrOH/water catalytic system was developed, which shows high catalytic activity in the Suzuki-Miyaura cross-coupling reactions of a diverse array of aryl and heteroaryl chlorides with Pd loadings down to 0.01 mol%.

Carboxyamido/carbene ligated palladium (II) complex: A versatile catalyst for the synthesis of aryl-substituted heteroarenes

Carboxy amido/carbene ligated Pd-complex catalyzed Suzuki-Miyaura cross-coupling of aryl-boronic acids with heteroaryl bromides is described. The protocol has a broad substrate scope that includes electron-rich, electron-deficient and sterically hindered arylboronic acids and heteroaryl bromides. The catalytic activity of the catalyst has been further investigated in the coupling of 2,6-dibromopyridine with arylboronic acids.

Nickel-Catalyzed Decarbonylative Coupling of Aryl Esters and Arylboronic Acids

A variety of functionalized biaryls can be accessed by coupling aryl and heteroaryl esters with boronic acids in Suzuki-Miyaura-type decarbonylative cross-coupling catalyzed by an affordable catalyst system composed of Ni(cod)2 and PCy3. The methodology is tolerant of a variety of functional groups and presents an attractive alternative to the use of palladium catalysis currently used in industry to acquire such bis(hetero)aryls, but also reveals challenges associated with nickel catalysis of esters in cross-coupling chemistry.

PIPERIDINE AND AZEPINE DERIVATIVES AS PROKINETICIN RECEPTOR MODULATORS

The present invention provides compounds of formula (I) and pharmaceutically acceptable salts thereof (Formula (I)) in which m, X, R1, R2, R3 and R5 are as defined in the specification, processes for their preparation, pharmaceutical compositions containing them and their use in therapy.

AMVN-initiated expedient synthesis of biaryls by the coupling reaction of unactivated arenes and heteroarenes with aryl iodides

The role of radical initiators AMVN and AIBN has been studied in the potassium tert-butoxide mediated biaryl coupling reaction of aryl iodides with unactivated arenes. Radical initiator AMVN promoted carbon-carbon bond formation expeditiously from aryl iodide having various groups such as amino, methoxy, fluoro, methyl, and trifluoromethyl and arenes in the presence of potassium tert-butoxide (4 equiv.) at 110 °C in 2-5 h. Substituted arenes such as toluene, xylene, anisole, and fluorobenzene also proceeded to form biaryls under AMVN-initiated reaction conditions. Moreover naphthalene, pyridine, pyrimidine, and pyridazine also coupled with aryl iodides and produced biaryls in 41-82% yields. It seems that AMVN initiates the formation of the aryl radical, which enters the radical chain reaction. The generated aryl radical may combine with the arene leading to a biaryl radical, which upon protonation gives the biphenyl radical anion and tert-butanol. The biphenyl radical anion finally reacts with the aryl iodide generating the aryl radical and thus completes the radical chain reaction with concomitant release of biphenyl.

Direct arylation of pyridines without the use of a transition metal catalyst

A method for achieving the direct arylation of pyridines with phenylhydrazine hydrochloride was developed in this study. This new reaction proceeds readily at room temperature without the use of any transition metal catalysts. This method allows rapid access to various arylated heterocycles that are more difficult to access through traditional methods.

Unexpected results of a SNAr-reaction. A novel synthetic approach to 1-arylthio-2-naphthols

1-(Phenylthio)-3-(pyridin-3-yl)-2-naphthol was obtained as an unexpected result of a nucleophilic aromatic substitution reaction of 3-(pyridine-3-yl) naphthalene-2-yl trifluoromethanesulfonate with thiophenol. This observation led to the discovery of an e

Palladium-catalyzed Suzuki cross-coupling of N′-tosyl arylhydrazines

The first palladium-catalyzed Suzuki cross-coupling of N′-tosyl arylhydrazines with various organoboron reagents has been developed for the preparation of biaryl compounds in high yields. N′-Tosyl arylhydrazine as a readily available and stable electrophile also demonstrated its generality in a number of coupling reactions. The Royal Society of Chemistry 2013.

General and highly efficient fluorinated-N-heterocyclic carbene-based catalysts for the palladium-catalyzed Suzuki-Miyaura reaction

A general and highly efficient trifluoromethylated-N-heterocyclic carbene (NHC)-based catalyst for the palladium-catalyzed Suzuki-Miyaura reaction was reported. In the presence of the catalyst, reactions of non-activated aryl chlorides and triflates with aryl boronic acids occurred at room temperature with good to excellent yields (63-98%). In addition, catalysts generated from a combination of Pd(OAc)2/imidazolium salt 6a is not only effective for the coupling of heteroaryl boronic acid with aryl halides and heteroaryl halides, but also efficient for coupling of other heteroaryl halides and heteroaryl boronic acids. Finally, the catalyst is highly effective for Suzuki-Miyaura reaction of aryl bromides and chlorides with 0.01-0.1 mol % loading if the temperature was raised at refluxed THF/H2O.