445264-61-9

Basic information

• Product Name: 2-Methoxyl-5-pyridineboronic acid pinacol ester
• Synonyms: 2-methoxyl-5-pyridineboronic acid pinacol ester;2-METHOXYPYRIDINE-5-BORONIC ACID PINACOL ESTER;2-METHOXY-5-PYRIDINEBORONIC ACID, PINACOL ESTER;2-METHOXY-5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PYRIDINE;6-METHOXYPYRIDINE-3-BORONIC ACID, PINACOL ESTER;2-Methoxy-5-pyridineboronic acid pinacol ester, 2-Methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine;6-Methoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine;2-Methoxy-5-(tetraMethyl-1,3,2-dioxaborolan-2-yl)pyridine
• CAS NO: 445264-61-9
• Molecular Formula: C₁₂H₁₈BNO₃
• Molecular Weight: 235.09
• Product Categories: CHIRAL CHEMICALS
• Mol File: 445264-61-9.mol

Chemical Properties

• Melting Point: 47-51 °C(lit.)
• Boiling Point: 102°C/0.08mmHg(lit.)
• Flash Point: 216 °F
• Appearance: /
• Density: 1.067 g/cm³
• Refractive Index: 1.5
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 3.39±0.12(Predicted)
• Water Solubility: Soluble in water
• CAS DataBase Reference: 2-Methoxyl-5-pyridineboronic acid pinacol ester(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Methoxyl-5-pyridineboronic acid pinacol ester(445264-61-9)
• EPA Substance Registry System: 2-Methoxyl-5-pyridineboronic acid pinacol ester(445264-61-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/38
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 445264-61-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Methoxyl-5-pyridineboronic acid pinacol ester is used as a key intermediate in the design and synthesis of oxazolidinone antibacterial agents. These agents are important in the development of new antibiotics to combat drug-resistant bacterial infections. 2-Methoxyl-5-pyridineboronic acid pinacol ester plays a crucial role in the formation of the oxazolidinone core structure, which is responsible for the antibacterial activity of these drugs.
Additionally, 2-Methoxyl-5-pyridineboronic acid pinacol ester is used as a synthetic building block in the synthesis of [3,2-b]pyridines. These heterocyclic compounds have potential applications in the development of various pharmaceuticals, including those with anti-cancer, anti-inflammatory, and anti-viral properties. The versatility of this compound in the synthesis of different drug candidates highlights its importance in the pharmaceutical industry.

InChI:InChI=1/C12H20BNO4/c1-11(2,15)12(3,4)18-13(16)9-6-7-10(17-5)14-8-9/h6-8,15-16H,1-5H3

Upstream product

• 61676-62-8 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 13472-85-0 2-methoxy-5-bromopyridine 
• 1628-89-3 2-methoxypyridine 
• 6628-77-9 6-methoxy-pyridin-3-ylamine 
• 73183-34-3 bis(pinacol)diborane 
• 1002759-87-6 1-(6-methoxypyridin-3-yl)butan-1-one 

Downstream Products

• 1002309-52-5 1-methyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyridin-2-one 
• 1272354-52-5 2-(6-methoxypyridin-3-yl)-5-phenyl-N-(pyridin-2-ylmethyl)quinazolin-4-amine 
• 1339925-49-3 (E)-methyl 3-(3-(N-(2-(6-methoxypyridin-3-yl)-4-morpholinothieno[3,2-d]pyrimidin-6-yl)sulfamoyl)phenyl)acrylate 
• 1431541-99-9 1-(4-{3-[6-(6-methoxy-pyridin-3-yl)-quinazolin-4-yl]-5-trifluoromethyl-benzoyl}-piperazin-1-yl)-ethanone 
• 1431542-43-6 3-[6-(6-methoxy-pyridin-3-yl)-quinazolin-4-yl]-benzoic acid ethyl ester 
• 1403396-70-2 8-({[tert-butyl(dimethyl)silyl]oxy}methyl)-3-{1-[4-(6-methoxypyridin-3-yl)phenyl]cyclopropyl}-8-methyl-5,6,8,9-tetrahydro[1,2,4]triazolo[4,3-d][1,4]thiazepine 
• 51834-97-0 6-methoxypyridine-3-ol 
• 431942-25-5 2-methoxy-5-(methoxymethoxy)pyridine 
• 1339928-25-4 CUDC-907 
• 381725-49-1 2-methoxy-5-(pyridin-2-yl)pyridine 

Relevant articles and documents

Transformations of Aryl Ketones via Ligand-Promoted C?C Bond Activation

The coupling of aromatic electrophiles (aryl halides, aryl ethers, aryl acids, aryl nitriles etc.) with nucleophiles is a core methodology for the synthesis of aryl compounds. Transformations of aryl ketones in an analogous manner via carbon–carbon bond activation could greatly expand the toolbox for the synthesis of aryl compounds due to the abundance of aryl ketones. An exploratory study of this approach is typically based on carbon–carbon cleavage triggered by ring-strain release and chelation assistance, and the products are also limited to a specific structural motif. Here we report a ligand-promoted β-carbon elimination strategy to activate the carbon–carbon bonds, which results in a range of transformations of aryl ketones, leading to useful aryl borates, and also to biaryls, aryl nitriles, and aryl alkenes. The use of a pyridine-oxazoline ligand is crucial for this catalytic transformation. A gram-scale borylation reaction of an aryl ketone via a simple one-pot operation is reported. The potential utility of this strategy is also demonstrated by the late-stage diversification of drug molecules probenecid, adapalene, and desoxyestrone, the fragrance tonalid as well as the natural product apocynin.

COMBINATION THERAPY WITH A PHOSPHOINOSITIDE 3-KINASE INHIBITOR WITH A ZINC BINDING MOIETY

The invention provides a method of treating cancer in a subject in need thereof, comprising administering to the subject: (a) a compound of Formula I: or a pharmaceutically acceptable salt thereof, wherein R is hydrogen or an acyl group; and (b) a PD-1 signaling inhibitor; wherein the compound of Formula I or pharmaceutically acceptable salt thereof and the PD-1 signaling inhibitor are administered in amounts which in combination are therapeutically effective. The invention further provides a pharmaceutical composition comprising a compound of Formula I or a pharmaceutically acceptable salt thereof, a PD-1 signaling inhibitor and a pharmaceutically acceptable carrier or excipient.

COMBINATION THERAPY WITH A PHOSPHOINOSITIDE 3-KINASE INHIBITOR WITH A ZINC BINDING MOIETY

The invention provides a method of treating cancer in a subject in need thereof, comprising administering to the subject: (a) a compound of Formula I: or a pharmaceutically acceptable salt thereof, wherein R is hydrogen or an acyl group; and (b) a BCL-2 inhibitor; wherein the compound of Formula I or pharmaceutically acceptable salt thereof and a BCL-2 inhibitor are administered in amounts which in combination are therapeutically effective. The invention further provides a pharmaceutical composition comprising a compound of Formula I or a pharmaceutically acceptable salt thereof, a BCL-2 inhibitor and a pharmaceutically acceptable carrier or excipient.

Phosphoinositide 3-kinase inhibitor with a zinc binding moiety

The invention provides a compound of Formula I, Pharmaceutical compositions comprising such compounds and the use of such compounds in the treatment of phosphoinositide 3-kinase related diseases and disorders such as cancer. The instant application further relates to the treatment of histone deacetylase related disorders and diseases related to both histone deacetylase and phosphoinositide 3-kinase.

2-methoxy-5-(pyridine-2-yl)pyridine synthesis method

The invention belongs to the field of medicinal chemistry and relates to a preparation technology of 2-methoxy-5-(pyridine-2-yl)pyridine as a perampanel intermediate. The preparation technology comprises that 5-bromo-2-methoxypyridine and bis(pinacolato)diboron undergo a reaction to produce 2-methoxypyridine-5-boronic acid pinacol ester and the 2-methoxypyridine-5-boronic acid pinacol ester and 2-halogenated pyridine undergo a reaction to produce 2-methoxy-5-(pyridine-2-yl)pyridine as a perampanel intermediate. The synthesis method solves the problem of a high catalyst cost, has the advantages of simple processes and low cost and is convenient for large scale production.

Identification of indole inhibitors of human hematopoietic prostaglandin D2 synthase (hH-PGDS)

Abstract Human H-PGDS has shown promise as a potential target for anti-allergic and anti-inflammatory drugs. Here we describe the discovery of a novel class of indole inhibitors, identified through focused screening of 42,000 compounds and evaluated using a series of hit validation assays that included fluorescence polarization binding, 1D NMR, ITC and chromogenic enzymatic assays. Compounds with low nanomolar potency, favorable physico-chemical properties and inhibitory activity in human mast cells have been identified. In addition, our studies suggest that the active site of hH-PGDS can accommodate larger structural diversity than previously thought, such as the introduction of polar groups in the inner part of the binding pocket.

Synthesis and anticancer effects evaluation of 1-alkyl-3-(6-(2-methoxy-3-sulfonylaminopyridin-5-yl)benzo[d]thiazol-2-yl)urea as anticancer agents with low toxicity

As a PI3K and mTOR dual inhibitor, N-(2-chloro-5-(2-acetylaminobenzo[d]thiazol-6-yl)pyridin-3-yl)-4-fluorophenylsulfonamide displays toxicity when orally administrated. In the present study, alkylurea moiety replaced the acetamide group in the compound an

METHODS FOR PRODUCING BORYLATED ARENES

Methods for the selective borylation of arenes, including arenes substituted with an electron-withdrawing group (e.g., 1-chloro-3-fluoro-2-substituted benzenes) are provided. The methods can be used, in some embodiments, to efficiently and regioselectivel

BASE METAL CATALYZED BORYLATION OF ARENES AND AROMMATIC HETEROCYCLES

In one aspect, cobalt complexes are described herein. In some embodiments, such cobalt complexes employ bis(phosphine) or bis(imine) ligand and are operable as catalysts for borylation of arenes and aromatic heterocycles.

Iridium-catalyzed C-H borylation of pyridines

The iridium-catalysed C-H borylation is a valuable and attractive method for the preparation of aryl and heteroaryl boronates. However, application of this methodology for the preparation of pyridyl and related azinyl boronates can be challenged by low reactivity and propensity for rapid protodeborylation, particularly for a boronate ester ortho to the azinyl nitrogen. Competition experiments have revealed that the low reactivity is due to inhibition of the active catalyst through coordination of the azinyl nitrogen lone pair at the vacant site on the iridium. This effect can be overcome through the incorporation of a substituent at C-2. Moreover, when this is sufficiently electron-withdrawing protodeborylation is sufficiently slowed to permit isolation and purification of the C-6 boronate ester. Following functionalization, reduction of the directing C-2 substituent provides the product arising from formal ortho borylation of an unhindered pyridine ring. This journal is the Partner Organisations 2014.