5958-00-9

Upstream product

• 110-86-1 pyridine 
• 90-04-0 2-methoxy-phenylamine 
• 51056-78-1 1-ethoxycarbonyl-pyridinium 
• 16750-63-3 2-methoxyphenylmagnesium bromide 
• 108770-97-4 4-pyridyl phenyl sulfoxide 
• 5720-06-9 2-Methoxyphenylboronic acid 
• 7379-35-3 4-chlorpyridine hydrochloride 
• 529-28-2 4-iodoanisol 
• 626-61-9 4-Chloropyridine 
• 578-57-4 2-bromoanisole 
• 93830-58-1 diethyl (pyridin-4-yl)borane 
• 15854-87-2 4-iodopyridine 
• 100-66-3 methoxybenzene 
• 19524-06-2 4-bromopyridine hydrochloride 

Downstream Products

• 86610-20-0 4-(2-hydroxyphenyl)pyridine 
• 81115-40-4 4-(2-hydroxyphenyl)-1-methylpyridinium iodide 
• 82212-04-2 1,2,3,4,5,6-hexahydro-4-(2-methoxyphenyl)pyridine hydrochloride 
• 81115-34-6 1-methyl-4-(2-(2-ethoxy-2-oxoethoxy)phenyl)pyridinium iodide 
• 81115-41-5 4-<2-(2-oxopropoxy)phenyl>pyridine 
• 86610-23-3 spiro<(2-(1-oxoethyl)benzofuran)-3(2H),4'(1'H)-(1-(phenyloxomethyl)pyridine)> 
• 86610-21-1 ethyl-2(4-pyridinyl)phenoxyacetate 
• 87308-05-2 2-[2-(Pyridin-4-yl)phenoxy]acetonitrile 
• 83420-56-8 4-(2-ethynylphenyl)pyridine 
• 1004760-10-4 4-(2-methoxyphenyl)pyridine hydrochloride 

Relevant academic research and scientific papers

Quantifying Through-Space Substituent Effects

The description of substituents as electron donating or withdrawing leads to a perceived dominance of through-bond influences. The situation is compounded by the challenge of separating through-bond and through-space contributions. Here, we probe the experimental significance of through-space substituent effects in molecular interactions and reaction kinetics. Conformational equilibrium constants were transposed onto the Hammett substituent constant scale revealing dominant through-space substituent effects that cannot be described in classic terms. For example, NO2 groups positioned over a biaryl bond exhibited similar influences as resonant electron donors. Meanwhile, the electro-enhancing influence of OMe/OH groups could be switched off or inverted by conformational twisting. 267 conformational equilibrium constants measured across eleven solvents were found to be better predictors of reaction kinetics than calculated electrostatic potentials, suggesting utility in other contexts and for benchmarking theoretical solvation models.

Palladium dichloride adduct of N,N-bis-(diphenylphosphanylmethyl)-2- aminopyridine: Synthesis, structure and catalytic performance in the decarboxylative cross-coupling of 4-picolinic acid with aryl bromide

Reaction of PdCl2 with N,N-bis-(diphenylphosphanylmethyl)-2- aminopyridine (bdppmapy) afforded a mononuclear complex [(bdppmapy)PdCl 2] (1). Compound 1 was characterized by elemental analysis, IR, 1H, 13C and 31P NMR, electrospray ion mass spectra (ESI-MS) and X-ray single crystal crystallography. The Pd(ii) center in 1 is chelated by bdppmapy, showing a cis-square planar geometry. With the assistance of additive Cu2O, complex 1 exhibited good catalytic activity toward the decarboxylative cross-coupling reactions between 4-picolinic acid and aryl bromides. In the presence of only 2 mol% catalyst, a family of 4-aryl-pyridines could be isolated in up to 83% yield.

Metal-free arylation of benzene and pyridine promoted by amino-linked nitrogen heterocyclic carbenes

An amino-linked nitrogen heterocyclic carbene (amino-NHC), 1-tBu, has been shown to mediate carbon-carbon coupling through the direct C-H functionalization of benzene and pyridine in the absence of a metal catalyst. Using EPR, the first spectroscopic evidence corroborating the single electron transfer mechanism for the metal-free carbon-carbon coupling manifold, as reported by others, is introduced.

Selenium dioxide-mediated methoxyhydroxylation of cyclic arylolefin

Selenium dioxide-mediated methoxyhydroxylation of cyclic arylolefin with the modest yields is described. This facile strategy was also used to synthesize several 4-arylpyridines, 3-hydroxy-4-arylpyridines, and 3,4-diarylpyridines. Crown Copyright

AZABENZIMIDAZOLYL COMPOUNDS

Compounds and pharmaceutically acceptable salts of the compounds are disclosed, wherein the compounds have the structure of Formula (I), as defined in the specification. Corresponding pharmaceutical compositions, methods of treatment, methods of synthesis, and intermediates are also disclosed.

BENZIMIDAZOLYL COMPOUNDS AS POTENTIATORS OF MGLUR2 SUBTYPE OF GLUTAMATE RECEPTOR

Compounds and pharmaceutically acceptable salts of the compounds are disclosed, wherein the compounds have the structure of Formula (I) as defined in the specification. Corresponding pharmaceutical compositions, methods of treatment, methods of synthesis, and intermediates are also disclosed.

Microwave-assisted Suzuki coupling reactions with an encapsulated palladium catalyst for batch and continuous-flow transformations

This article describes the design, optimisation and development of a Suzuki cross-coupling protocol mediated by an efficient palladium-en-capsulated catalyst (Pd EnCat) under microwave irradiation. The methodology has been used in both batch mode for classical library preparation and in continuous-flow applications furnishing multigram quantities of material. Described is a method that uses direct focused microwave heating whilst applying an external cooling source. This enables a lower than normal bulk temperature to be maintained throughout the reaction period leading to significant improvements in the overall yield and purity of the reaction products. Additional aspects of this novel heating protocol are discussed in relation to the prolonged lifetime and enhanced reactivity of the immobilised catalyst system.

Radical dearomatization of arenes and heteroarenes

The stannane-mediated benzeneselenol-catalyzed addition of aryl iodides to a range of arenes and aromatic hetereocycles has been studied. With furan, thiophene, and several carbocyclic arenes, the addition takes place with quenching of the adduct radical by the catalytic selenol leading to moderate yields of aryl-dihydroarenes. With nitrogen heterocycles, on the other hand, it was not possible to suppress aromatization of the adduct radical and fully aromatized products were isolated. Aryl iodides bearing hydrogen bond donating groups in the ortho-position add to nitrogen heterocycles with high selectivity ortho- to the nitrogen, affording a simple one-step synthesis of potential chelating ligands. While 2-iodophenol is an excellent aryl radical source in these reactions, the homologous 1-iodo-2-naphthol fails owing to its reaction with diphenyl diselenide, which gives 1-phenylseleno-2-naphthol in high yield.

Pyridino-directed lithiation of anisylpyridines: New access to functional pyridylphenols

The lithiation of nine anisylpyridines has been studied. While usual reagents did not react or gave addition products on pyridine ring, the BuLi-LiDMAE (LiDMAE=Me2N(CH2)2OLi) superbase induced exclusive pyridino directed metallation. The usefulness of this new reaction allowed the efficient preparation of a range of alpha functional pyridylphenols. A successful subsequent cyclisation of an appropriate isomer into corresponding benzofuropyridine was also performed.

Direct synthesis of heterobiaryls by radical addition to pyridine: Expeditious synthesis of chelating ligands

The addition of aryl radicals to pyridine may be affected in moderate yield on exposure of aryl iodides to tributyltin hydride, AIBN, and diphenyl diselenide in hot pyridine. Mixtures of ortho-, meta-, and para-aryl substituted pyridines are typically obtained. When the iodide is ortho-substituted with a hydrogen bond donor, such as o-iodophenol, significantly improved selectivity for ortho-substituted pyridines, with potential as bidentate chelating ligands, is obtained.