25363-50-2

Basic information

• Product Name: 3-methyl-2-(4-methoxyphenyl)pyridine
• Synonyms: 3-methyl-2-(4-methoxyphenyl)pyridine
• CAS NO: 25363-50-2
• Molecular Formula: C₁₃H₁₃NO
• Molecular Weight: 199
• Mol File: 25363-50-2.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-methyl-2-(4-methoxyphenyl)pyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 3-methyl-2-(4-methoxyphenyl)pyridine(25363-50-2)
• EPA Substance Registry System: 3-methyl-2-(4-methoxyphenyl)pyridine(25363-50-2)

Safety Data

• Hazardous Substances Data: 25363-50-2(Hazardous Substances Data)

Upstream product

• 14401-92-4 3-methylpyridinium chloride 
• 104-94-9 4-methoxy-aniline 
• 18368-76-8 2 chloro-3-methylpyridine 
• 117446-06-7 3-Methyl-2-(phenylmethylthio)-pyridine 
• 5720-07-0 4-methoxyphenylboronic acid 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 3430-17-9 2-bromo-3-picoline 
• 154447-02-6 3-methylpyridin-2-yl trifluoromethanesulfonate 
• 108-99-6 3-Methylpyridine 
• 19501-58-7 4-methoxyphenylhydrazine hydrochloride 
• 696-62-8 para-iodoanisole 
• 13139-86-1 4-methoxyphenyl magnesium bromide 
• 171364-79-7 2-(4-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 

Downstream Products

• 1240787-18-1 (E)-2-(4-methoxy-2-(1-(trimethylsilyl)hex-1-en-2-yl)phenyl)-3-methylpyridine 
• 1240787-15-8 (E)-2-(2-(2,2-dimethyloct-3-en-4-yl)-4-methoxyphenyl)-3-methylpyridine 
• 1240787-12-5 (E)-2-(2-(hex-2-en-2-yl)-4-methoxyphenyl)-3-methylpyridine 
• 1240787-13-6 (E)-2-(2-(hex-2-en-3-yl)-4-methoxyphenyl)-3-methylpyridine 
• 1240787-14-7 (E)-2-(4-methoxy-2-(4-methylpent-2-en-2-yl)phenyl)-3-methylpyridine 
• 1240787-06-7 (E)-2-(4-methoxy-2-(oct-4-en-4-yl)phenyl)-3-methylpyridine 
• 1240787-16-9 (Z)-2-(2-(1,4-bis(trimethylsilyl)but-2-en-2-yl)-4-methoxyphenyl)-3-methylpyridine 
• 1240787-17-0 (E)-2-(2-(1,8-bis(benzyloxy)oct-4-en-4-yl)-4-methoxyphenyl)-3-methylpyridine 
• 1607824-53-2 2-(5-methoxy-2-(3-methylpyridin-2-yl)phenyl)isoindoline-1,3-dione 
• 502159-59-3 6-[1-(2,4-dichloro-phenyl)-cyclopropyl]-2-(4-methoxy-phenyl)-3-methyl-pyridine 
• 502159-58-2 6-[1-(2,4-dichloro-phenyl)-vinyl]-2-(4-methoxy-phenyl)-3-methyl-pyridine 
• 502159-57-1 (2,4-dichloro-phenyl)-[6-(4-methoxy-phenyl)-5-methyl-pyridin-2-yl]-methanone 

Relevant articles and documents

Desulfonative Suzuki–Miyaura Coupling of Sulfonyl Fluorides

Sulfonyl fluorides have emerged as powerful “click” electrophiles to access sulfonylated derivatives. Yet, they are relatively inert towards C?C bond forming transformations, notably under transition-metal catalysis. Here, we describe conditions under which aryl sulfonyl fluorides act as electrophiles for the Pd-catalyzed Suzuki–Miyaura cross-coupling. This desulfonative cross-coupling occurs selectively in the absence of base and, unusually, even in the presence of strong acids. Divergent one-step syntheses of two analogues of bioactive compounds showcase the expanded reactivity of sulfonyl fluorides to encompass both S?Nu and C?C bond formation. Mechanistic experiments and DFT calculations suggest oxidative addition occurs at the C?S bond followed by desulfonation to form a Pd-F intermediate that facilitates transmetalation.

Base-Activated Latent Heteroaromatic Sulfinates as Nucleophilic Coupling Partners in Palladium-Catalyzed Cross-Coupling Reactions

Heteroaromatic sulfinates are effective nucleophilic reagents in Pd0-catalyzed cross-coupling reactions with aryl halides. However, metal sulfinate salts can be challenging to purify, solubilize in reaction media, and are not tolerant to multi-step transformations. Here we introduce base-activated, latent sulfinate reagents: β-nitrile and β-ester sulfones. We show that under the cross-coupling conditions, these species generate the sulfinate salt in situ, which then undergo efficient palladium-catalyzed desulfinative cross-coupling with (hetero)aryl bromides to deliver a broad range of biaryls. These latent sulfinate reagents have proven to be stable through multi-step substrate elaboration, and amenable to scale-up.

Stereodivergent Synthesis of Alkenylpyridines via Pd/Cu Catalyzed C-H Alkenylation of Pyridinium Salts with Alkynes

The first Pd/Cu catalyzed selective C2-alkenylation of pyridines with internal alkynes has been developed via the pyridinium salt activation strategy. Importantly, the configuration of the product alkenylpyridines could be tuned by the choice of the proper N-alkyl group of the pyridinium salts, thus allowing for both the Z- and E-alkenylpyridines synthesized with good regio- and stereoselectivity. A plausible mechanism was proposed based on the Hammett study and KIE experiment.

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.

Practical Ni-Catalyzed Cross-Coupling of Unsaturated Zinc Pivalates with Unsaturated Nonaflates and Triflates

A practical nickel-catalyzed cross-coupling of (hetero)aryl or alkynylzinc pivalates with various unsaturated nonaflates or triflates is described. Organozinc pivalates allow these cross-couplings to take place with high yields and a low catalyst loading (0.5 mol %). Couplings with (E)- and (Z)-alkenyl triflates proceed with retention of configuration.

Palladium-Catalyzed Electrochemical C-H Alkylation of Arenes

Palladium-catalyzed electrochemical C-H functionalization reactions have emerged as attractive tools for organic synthesis. This process offers an alternative to conventional methods that require harsh chemical oxidants. However, this electrolysis requires divided cells to avoid catalyst deactivation by cathodic reduction. Herein, we report the first example of palladium-catalyzed electrochemical C-H alkylation of arenes using undivided electrochemical cells in water, thereby providing a practical solution for the introduction of alkyl groups into arenes.

Palladium catalyzed ortho-C-H-acylation of 2-arylpyridines using phenylacetylenes and styrene epoxide

A palladium-catalyzed ortho-C-H-acylation of 2-arylpyridine using phenylacetylenes and styrene epoxide as the acylated reagents was developed. With the employment of tert-butyl hydroperoxide (TBHP) as the oxidant and a phosphorous ligand, the protocol generates corresponding aryl ketones in moderated to good yields with high regioselectivity and good functional group compatibility.

Scope of Successive C-H Functionalizations of the Methyl Group in 3-Picolines: Intramolecular Carbonylation of Arenes to the Metal-Free Synthesis of 4-Azafluorenones

A transition-metal-free, t-BuOOH mediated intramolecular carbonylation of arenes in 2-aryl-3-picolines via oxidative C-H functionalizations of the methyl group has been developed, providing an expedient synthesis of 4-azafluorenones. Distinct from the current literature wherein methylarenes have been used as acylating agents, 2-aryl-3-picolines in this study are transformed into aldehydes, which give 4-azafluorenones upon rapid intramolecular acylation. The study demonstrates the first example of intramolecular carbonylation of arenes utilizing a methyl group as latent carbonyl functionality.

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.

Direct arylation of n-heteroarenes with aryldiazonium salts by photoredox catalysis in water

A highly effective visible light-promoted "radical-type" coupling of N-heteroarenes with aryldiazonium salts in water has been developed. The reaction proceeds at room temperature with [Ru(bpy)3]Cl 2×6 H2O as a photosensit