4385-63-1

Usage

Structure

Pyridine derivative with a 2-(4-methoxyphenyl) and 6-methyl substituent

Usage

Building block in the synthesis of pharmaceuticals and agrochemicals, research chemical in the development of new drugs and materials

Physical state

Solid at room temperature

Handling and storage

Dry, cool environment

Safety precautions

Potential health and safety hazards if mishandled

Upstream product

• 2867-59-6 2-aminobutanol 
• 3319-15-1 rac-1-(4-methoxyphenyl)-ethanol 
• 281221-71-4 6-methylpyridine-2-sulfonyl chloride 
• 5720-07-0 4-methoxyphenylboronic acid 
• 109-06-8 α-picoline 
• 18368-57-5 2-mercapto-6-methylpyridine 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 5315-25-3 2-bromo-6-methylpyridine 
• 696-62-8 para-iodoanisole 
• 10412-98-3 5-oxohexanenitrile 
• 934-60-1 6-methyl-2-pyridinecarboxylic acid 
• 598-32-3 2-hydroxy-3-butene 
• 96155-57-6 1-(4-methoxyphenyl)ethanone O-acetyl oxime 
• 14401-91-3 picoline hydrochloride 

Relevant academic research and scientific papers

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.

Direct C-H Arylation and Alkylation of Electron-Deficient Heteroaromatic Compounds with Organozinc Reagents

A direct and convenient method for the C-H arylation and alkylation of electron-deficient N-heteroarenes with readily available organozinc reagents has been developed. This transformation could be readily performed in the absence of a transition-metal catalyst and external oxidants, affording a wide range of substituted heteroarenes with good functional group tolerance in good to excellent yields. The developed simple protocol is scalable to the gram level and suitable for late-stage modification of bioactive molecules and drugs.

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.

Borenium-Catalyzed Reduction of Pyridines through the Combined Action of Hydrogen and Hydrosilane

Mesoionic carbene-stabilized borenium ions efficiently reduce substituted pyridines to piperidines in the presence of a hydrosilane and a hydrogen atmosphere. Control experiments and deuterium labeling studies demonstrate reversible hydrosilylation of the pyridine, enabling full reduction of the N-heterocycle under milder conditions. The silane is a critical reaction component to prevent adduct formation between the piperidine product and the borenium catalyst.

Formate-Mediated Cross-Electrophile Reductive Coupling of Aryl Iodides and Bromopyridines

Two catalytic systems for the formate-mediated cross-electrophile reductive coupling of aryl iodides with 6-bromopyridines are described. Using homogenous rhodium or heterogeneous palladium catalysts, the products of reductive biaryl cross-coupling could

Palladium-Catalyzed Cascade Reactions of I-Ketonitriles with Arylboronic Acids: Synthesis of Pyridines

This study presents the first example of the Pd-catalyzed cascade reactions of 5-oxohexanenitrile with arylboronic acids, affording important synthon 2-methylpyridines that can be further translated through C(sp3)-H functionalization to construct pyridine derivatives. Furthermore, this chemistry allows 5-oxo-5-Arylpentanenitrile to react with arylboronic acids to provide unsymmetrical 2,6-diarylpyridines. This protocol paves the way for the practical and atom economical syntheses of valuable pyridines with broad functional groups in moderate to excellent yields under mild conditions.

NNN-Ruthenium Catalysts for the Synthesis of Pyridines, Quinolines, and Pyrroles by Acceptorless Dehydrogenative Condensation

The bidentate ruthenium complex (HO-C5H3N-CO-C5H3N-C5H4N)Ru(CO)2Cl2 (2) could transform to a tridentate product (HO-C5H3N-CO-C5H3N-C5H4N)Ru(CO)Cl2 (3), which further reacted with CH3ONa in the presence of PPh3 to convert to two complexes [(OC5H3N-CO-C5H3N-C5H4N)Ru(PPh3)2(CO)]Cl- (4) and [(OC5H3N-CO-C5H3N-C5H4N)Ru(PPh3)(CO)Cl] (5), via -OH deprotonation. The catalytic coupling cyclizations of secondary alcohols with amino alcohols were investigated, and complex 3 exhibited the highest activity. The coupling reactions proceeded in air with only 0.2 mol % catalyst loading and had a broad scope for the synthesis of pyridines, quinolones, and pyrroles.

Palladium-Catalyzed Decarbonylative Cross-Coupling of Azinecarboxylates with Arylboronic Acids

The first palladium-catalyzed decarbonylative coupling of phenyl 2-azinecarboxylates and arylboronic acids is presented. The key for the development of this decarbonylative coupling is the use of Pd/dcype as a catalyst. A wide range of 2-azinecarboxylates can undergo the present coupling reaction to afford 2-arylazines. By combination with previously reported nickel-catalyzed decarbonylative coupling, we achieved a chemoselective sequential decarbonylative coupling of pyridine dicarboxylate to synthesize 2,4-diarylpyridine.

TETRAZOLINONE COMPOUNDS AND APPLICATIONS THEREOF

A tetrazolinone compound represented by formula (1): wherein Q represents a 6-membered aromatic heterocyclic group optionally having one or more atoms or groups selected from Group P1, provided that a heteroatom constituting the heterocyclic gr

Palladium-catalyzed Heck-type reaction of oximes with allylic alcohols: Synthesis of pyridines and azafluorenones

We describe herein a palladium-catalyzed Heck-type reaction of O-acetyl ketoximes and allylic alcohols to synthesise pyridines. This protocol allows the robust synthesis of pyridines and azafluorenones in good to excellent yields with tolerance of various functional groups under mild conditions. The reaction is supposed to go through an oxidative addition of oximes to palladium(0) complexes, generating an alkylideneamino-palladium(ii) species, which is utilized as a key intermediate to capture the nonbiased alkenes for carbon-carbon bond formation.