4634-13-3

Usage

Uses

Used in Pharmaceutical Industry:
METHYL 6-PHENYLNICOTINATE is used as a pharmaceutical intermediate for the synthesis of various drugs, leveraging its anti-inflammatory and analgesic properties to develop new treatments for inflammatory and painful conditions.
Used in Food Industry:
METHYL 6-PHENYLNICOTINATE is used as a flavoring agent for its pleasant aroma, enhancing the sensory experience of food products.

InChI:InChI=1/C13H11NO2/c1-16-13(15)11-7-8-12(14-9-11)10-5-3-2-4-6-10/h2-9H,1H3

Upstream product

• 73781-91-6 6-Chloronicotinic acid methyl ester 
• 98-80-6 phenylboronic acid 
• 108-86-1 bromobenzene 
• 26218-78-0 methyl 6-bromonicotinate 
• 1211000-48-4 (+/-)-(E)-methyl 3-(1-phenylprop-2-ynyloxy)acrylate 
• 67-56-1 methanol 
• 63056-20-2 2-phenyl-5-pyridinecarboxaldehyde 
• 1228932-02-2 (E)-methyl 2-(azidomethyl)-5-phenylpent-2-en-4-ynoate 
• 6311-35-9 6-bromonicotinic acid 
• 17874-79-2 pyridine-2,5-dicarboxylic acid 5-methyl ester 
• 71-43-2 benzene 
• 591-50-4 iodobenzene 
• 27531-48-2 (+/-)-methyl 1-benzyl-6-phenyl-1,6-dihydropyridine-3-carboxylate 
• 5123-13-7 5,5-dimethyl-2-phenyl-1,3,2-dioxaborinane 

Downstream Products

• 4634-09-7 2-phenyl-5-hydroxymethylpyridine 
• 63056-20-2 2-phenyl-5-pyridinecarboxaldehyde 
• 179055-41-5 Cycloheptyl-(6-phenyl-pyridin-3-ylmethyl)-amine 
• 29051-44-3 6-phenylpyridine-3-carboxylic acid 
• 1285665-65-7 C₂₇H₂₄N₂O₄S 

Relevant academic research and scientific papers

Light-Promoted Dearomative Cross-Coupling of Heteroarenium Salts and Aryl Iodides via Nickel Catalysis

Partially saturated nitrogen heterocycles are versatile building blocks for the preparation of other nitrogen heterocycles. For example, dihydropyridines can be converted to pyridines, tetrahydropyridines, and piperidines through oxidation, reduction, and functionalization reactions, respectively. Dearomatization of heteroarenes is an attractive approach for the synthesis of partially saturated heterocycles such as dihydropyridines due to the wide availability of heteroarenes. Significant research efforts have been dedicated to the addition of nucleophiles to various heteroarenium salts in this direction using organoboron or organometallic reagents. The availability of organoboron and organometallic coupling partners has been an important limitation to this chemistry. Direct coupling of electrophiles with heteroareniums could significantly improve the scope of these dearomatization reactions due to the wider availability of electrophiles compared to nucleophiles such as organoboron and organometallic reagents. Herein, we report the coupling of aryl iodides with pyridinium and related heteroarenium salts catalyzed by Ni/bpp and an Ir photocatalyst using Zn as a terminal reductant. This methodology tolerates a wide range of functional groups and allows the coupling of aryl and heteroaryl iodides, thus significantly expanding the scope of nitrogen heterocycle scaffolds that could be prepared through dearomatization of heteroarenes. The reaction products have been further functionalized to prepare various nitrogen heterocycles. Initial mechanistic studies indicate that the reaction described herein goes through a unique mechanism involving dimers of dihydroheteroarenes.

Robust Packing of a Self-Assembling Iridium Complex via Endocytic Trafficking for Long-Term Lysosome Tracking

Live cell imaging of lysosome positioning and motility is critical to studying lysosome status and function for pharmacological interventions. To create a super stable lysosomal probe for long-term live cell imaging, we have designed and synthesized an aromatic-peptide-conjugated cyclometalated iridium(III) complex that emits light via π–π stacking oriented self-assembly in water at extremely low concentration. Through endocytic trafficking, self-assemblies are transformed from nanoparticles into sturdily packed networks that are stabilized in lysosomal acidic environment. Upon short time/low dose treatment of the iridium complex at passage 0, live cell lysosomal tracking is applicable beyond the 14th passage of cells with high labelling rate and a mild decline in luminescence intensity. The illuminated lysosomes are trackable using super-resolution imaging to study their response to cellular processes.

NEW HETEROARYL AMIDE DERIVATIVES AS SELECTIVE INHIBITORS OF HISTONE DEACETYLASES 1 AND/OR 2 (HDAC1-2)

The present invention relates to novel heteroaryl amide derivatives of formula (1) as selective inhibitors of histone deacetylase 1 and 2 (hdac1-2) to processes for their preparation, to pharmaceutical compositions comprising said compounds and to the use of said compounds for manufacturing a medicament for the treatment of pathological conditions or diseases that can improve by inhibition the activity of histone deacetylase class I, particularly HDAC1 and HDAC2, such as cancer, neurodegenerative diseases, Infectious diseases, inflammatory diseases, heart failure and cardiac hypertrophy, diabetes, polycystic kidney disease, sickle cell disease and β-thalassemia disease and to methods for the treatment of the disesases mentioned above.

Exhaustive Reduction of Esters Enabled by Nickel Catalysis

We report a one-step procedure to directly reduce unactivated aryl esters into their corresponding tolyl derivatives. This is achieved by an organosilane-mediated ester hydrosilylation reaction and subsequent Ni/NHC-catalyzed hydrogenolysis. The resulting conditions provide a direct and efficient alternative to multi-step procedures for this transformation that often require the use of hazardous metal hydrides. Applications in the synthesis of -CD3-containing products, derivatization of bioactive molecules, and chemoselective reduction in the presence of other C-O bonds are demonstrated.

Regio- and Stereoselective Synthesis of Functionalized Dihydropyridines, Pyridines, and 2H-Pyrans: Heck Coupling of Monocyclopropanated Heterocycles

A palladium-catalyzed coupling between aryl halides and monocyclopropanated pyrroles or furans has been developed, leading to valuable six-membered N- and O-heterocycles. As the key step, a selective cleavage of the non-activated endocyclic C?C bond of the 2-heterobicyclo-[3.1.0]hexane framework is achieved. The developed method offers access to highly functionalized piperidines, pyridines, and pyrans that are challenging to access by traditional methods.

Transition-Metal-Free Decarboxylative Arylation of 2-Picolinic Acids with Arenes under Air Conditions

A facile, transition-metal-free, and direct decarboxylative arylation of 2-picolinic acids with simple arenes is described. The oxidative decarboxylative arylation of 2-picolinic acids with arenes proceeds readily via N-chloro carbene intermediates to afford 2-arylpyridines in satisfactory to good yields under transition-metal-free conditions. This new type of decarboxylative arylation is operationally simple and scalable and exhibits high functional-group tolerance. Various synthetically useful functional groups, such as halogen atoms, methoxycarbonyl, and nitro, remain intact during the decarboxylative arylation of 2-picolinic acids.

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.

Non-transition metal-catalyzed 2-phenylpyridine compound synthesis method

The invention relates to a pharmaceutical and chemical intermediate preparation method, in particular to a non-transition metal-catalyzed 2-phenylpyridine compound synthesis method. A 2-phenylpyridine compound serves as an important component of a plurality of pharmacologically active molecules and bioactive molecules, has important application value in the fields of organic synthesis, pharmaceutical chemistry and the like, and is broad in market prospect. According to the non-transition metal-catalyzed 2-phenylpyridine compound synthesis method, namely a non-transition metal-catalyzed 2-phenylpyridine derivative synthesis method, pyridine-2-formic acid and benzene are adopted as raw materials; and under the presence of one or more alkalis and free radical initiators, the 2-phenylpyridine compound is synthesized in the mild condition. The non-transition metal-catalyzed 2-phenylpyridine compound synthesis method provided by the invention has the advantages that the steps are simple, the raw materials are easy to obtain, the reaction condition is mild, as well as the use value and the social and economic benefits are relatively great.

Cobalt-Catalyzed Biaryl Couplings via C-F Bond Activation in the Absence of Phosphine or NHC Ligands

A highly general and selective Co-catalyzed biaryl coupling through C-F cleavage under phosphine or NHC-free conditions was described. A broad range of aryl fluorides including unactivated fluorides as well as those with sensitive functionalities could couple with various Ti(OEt)4-mediated aryl Grignard reagents with high selectivity under the catalysis of CoCl2/DMPU. Importantly, selective C-F bond activation couplings between two types of fluorines (difluorinated aromatics and on two different coupling partners) and in the presence of C-Cl or C-Br bonds could also be achieved.

Direct ortho-Arylation of Pyridinecarboxylic Acids: Overcoming the Deactivating Effect of sp2-Nitrogen

Direct arylations of pyridines are challenging transformations due to the high Lewis basicity of the sp2-nitrogen. The use of carboxylates as directing groups is reported, facilitating the Pd-catalyzed C-H arylation of this difficult class of substrates. This methodology allows regioselective C3/C4 arylation, without the need to use solvent quantities of the pyridine, and using low-cost chloro- and bromoarenes as coupling partners. Furthermore, carboxylates could be employed as traceless directing groups through a one-pot C-H arylation/Cu(I)-mediated decarboxylation sequence, thereby accessing directing-group-free pyridine biaryls.