458532-84-8

Usage

Uses

Used in Organic Synthesis:
2-Chloropyridine-4-boronic acid pinacol ester is used as a building block for the synthesis of various complex organic molecules. Its reactivity and stability contribute to the formation of carbon-carbon bonds, facilitating the creation of diverse chemical structures.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 2-Chloropyridine-4-boronic acid pinacol ester is used as a key intermediate in the development of new drugs. Its ability to participate in Suzuki-Miyaura cross-coupling reactions allows for the synthesis of biologically active compounds with potential therapeutic applications.
Used in Suzuki-Miyaura Cross-Coupling Reactions:
2-Chloropyridine-4-boronic acid pinacol ester is used as a versatile reagent in Suzuki-Miyaura cross-coupling reactions for the formation of carbon-carbon bonds. This application is crucial in the synthesis of complex organic molecules, including those with potential pharmaceutical relevance, due to its wide applicability and the mild reaction conditions it allows.

InChI:InChI=1/C11H15BClNO2/c1-10(2)11(3,4)16-12(15-10)8-5-6-14-9(13)7-8/h5-7H,1-4H3

Upstream product

• 73583-37-6 2-chloro-4-bromopyridine 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 109-09-1 2-chloropyridine 
• 73183-34-3 bis(pinacol)diborane 
• 458532-96-2 2-chloropyridine-4-boronic acid 
• 67975-91-1 2-chloro-4,4,5,5,-tetramethyl-1,3,2-dioxaboralane 

Downstream Products

• 17368-12-6 2-chloropyridin-4-ol 
• 862722-99-4 4-(2-chloro-4-pyridinyl)-N-(3-methoxybenzyl)benzamide 
• 42260-39-9 2-chloro-4-(phenyl)pyridine 

Relevant academic research and scientific papers

para-Selective C?H Borylation of (Hetero)Arenes by Cooperative Iridium/Aluminum Catalysis

para-Selective C?H borylation of benzamides and pyridines has been achieved by cooperative iridium/aluminum catalysis. A combination of iridium catalysts commonly employed for arene C?H borylation and bulky aluminum-based Lewis acid catalysts provides an unprecedented strategy for controlling the regioselectivity of C?H borylation to give variously substituted (hetero)arylboronates, which are versatile synthetic intermediates for complex multi-substituted aromatic compounds.

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.

4-Azolylphenyl isoxazoline insecticides acting at the GABA gated chloride channel

Isoxazoline insecticides have been shown to be potent blockers of insect GABA receptors with excellent activity on a broad pest range, including Lepidoptera and Hemiptera. Herein we report on the synthesis, biological activity and mode-of-action for a class of 4-heterocyclic aryl isoxazoline insecticides.

Asymmetric synthesis of 1-heteroaryl-1-arylalkyl tertiary alcohols and 1-pyridyl-1-arylethanes by lithiation-borylation methodology

The synthesis of highly enantioenriched α-heterocyclic tertiary alcohols has been achieved via lithiation-borylation of a configurationally stable lithiated carbamate and heterocyclic pinacol boronic esters followed by oxidation. Protodeboronation of the α-heterocyclic tertiary boronic esters using TBAF·3H2O or CsF gave highly enantioenriched 1-pyridyl-1-arylethanes in high er.

Synthesis of biaryls through a one-pot tandem borylation/Suzuki-Miyaura cross-coupling reaction catalyzed by a palladacycle

The tricyclohexylphosphane adduct of cyclopalladated ferrocenylimine I exhibited high catalytic activity in the one-pot borylation/Suzuki-Miyaura coupling (BSC) reaction with low catalyst loading (2 mol-%). Various biaryls were obtained in good to excellent yields for 37 examples. This process was applied to aryl and heteroaryl halides (Br and Cl) containing a variety of functional groups and did not require an excess amount of phosphane ligand and the addition of the palladium catalyst in the second step. Cyclopalladated ferrocenylimine I exhibited high catalytic activity in the borylation/Suzuki- Miyaura coupling (BSC) reaction with low catalyst loading. Various unsymmetrical biaryls were obtained ingood to excellent yields in one pot. This protocol was applied to aryl and heteroaryl halides (Br and Cl) containing a variety of functional groups without adding catalyst in the second step. Copyright

Selective inhibitors of rock protein kinase and uses thereof

Described herein are compounds that are useful as ROCK inhibitors. These compounds, and pharmaceutically acceptable compositions thereof, are useful for treating or lessening the severity of a variety of disorders, including cardiovascular, inflammatory,

Synthesis of novel halopyridinylboronic acids and esters. Part 3: 2, or 3-Halopyridin-4-yl-boronic acids and esters

This paper describes a general method for the synthesis and the isolation of novel 2, or 3-halopyridin-4-yl-boronic acids and esters 12-14, 18-20. These compounds are prepared taking in account a regioselective halogen-metal exchange using nBuLi or direct