223463-14-7

Usage

Uses

Used in Organic Synthesis:
2-Bromopyridine-5-boronic acid is used as a reactant in iterative cross-coupling reactions for the synthesis of non-cytotoxic terpyridines. These terpyridines have potential applications in various fields, such as coordination chemistry, supramolecular chemistry, and as ligands for metal complexes.
Used in Pharmaceutical Industry:
2-Bromopyridine-5-boronic acid is used as a building block in the Garlanding approach for the synthesis of phenyl-pyridyl scaffolds. These scaffolds are important in the development of new pharmaceutical compounds, as they can exhibit a range of biological activities, such as anticancer, antiviral, and antibacterial properties.
Used in Chemical Industry:
2-Bromopyridine-5-boronic acid is used as a reactant in cyanation reactions for the synthesis of aromatic nitriles. Aromatic nitriles are valuable intermediates in the production of various chemicals, such as pharmaceuticals, agrochemicals, and dyes.
Used in Cross-Coupling Reactions:
2-Bromopyridine-5-boronic acid is used as a reactant in Suzuki-Miyaura cross-coupling reactions with dihalopyridines and dihalobipyridines. This reaction allows for the formation of new carbon-carbon bonds, leading to the synthesis of a wide range of pyridine-containing compounds with potential applications in various fields.
Used in Petasis Boronic Mannich Reaction:
2-Bromopyridine-5-boronic acid is used as a reactant in the Petasis boronic Mannich reaction, which is a three-component reaction involving an amine, an aldehyde, and a boronic acid. This reaction provides a convenient method for the synthesis of β-amino carbonyl compounds, which are important building blocks in the preparation of pharmaceuticals, agrochemicals, and other organic compounds.

InChI:InChI=1/C5H5BBrNO2/c7-5-2-1-4(3-8-5)6(9)10/h1-3,9-10H

Upstream product

• 624-28-2 2,5-dibromopyridine 
• 5419-55-6 Triisopropyl borate 
• 20511-12-0 2-amino-5-iodopyridine 
• 504-29-0 2-aminopyridine 
• 73290-22-9 2-bromo-5-iodo-pyridine 

Downstream Products

• 107351-82-6 2-bromo-5-phenyl-pyridine 
• 942189-65-3 2-(6-bromo-pyridin-3-yl)-pyrimidine 
• 342618-54-6 6'-bromo-[2,3']bipyridinyl 
• 109-04-6 2-bromo-pyridine 
• 4487-59-6 2-bromo-5-nitropyridine 
• 19755-53-4 2-bromo-3-nitropyridine 
• 16420-30-7 2-bromo-3,5-dinitro-pyridine 
• 1339154-55-0 1-{[4-(6-bromopyridin-3-yl)benzyl]methylamino}-2-(2,4-difluorophenyl)3-(1H-1,2,4-triazol-1-yl)propan-2-ol 
• 1339154-62-9 2-(2,4-difluorophenyl)-1-({4-[6-(diphenylmethylideneamino)-pyridin-3-yl]benzyl}methylamino)-3-(1H-1,2,4-triazol-1-yl)propan-2-ol 
• 1339154-63-0 1-{[4-(6-aminopyridin-3-yl)benzyl]methylamino}-2-(2,4-difluorophenyl)-3-(1H-1,2,4-triazol-1-yl)propan-2-ol 
• 1339154-67-4 N-{5-[4-({[2-(2,4-difluorophenyl)-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propyl]methylamino}methyl)phenyl]pyridin-2-yl}methanesulfonamide 
• 1339154-68-5 N-{5-[4-({[2-(2,4-difluorophenyl)-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propyl]methylamino}methyl)phenyl]pyridin-2-yl}benzenesulfonamide 
• 1400740-37-5 N-{2-[4-(6-bromo-pyridin-3-yl)-phenyl]-1-fluoromethyl-2-hydroxy-ethyl}-2,2-dichloro-acetamide 

Relevant academic research and scientific papers

ANTIMICROBIAL AGENTS

The present invention relates to the field of anti-infective, anti-proliferative, anti-inflammatory, and prokinetic agents. More particularly, the invention relates to substituted aromatic compounds useful as therapeutic agents.

Synthesis of dihalo bi- and terpyridines by regioselective Suzuki-Miyaura cross-coupling reactions

This paper describes an efficient and regioselective synthetic route leading to new dihalobi- and terpyridines. We developed a strategy based on regioselective sequence of Suzuki-Miyaura cross-coupling reactions between bromopyridyl boronic acids and dihalopyridines and dihalobipyridines. The study of the influence of the nature and the position of the halogen atoms leads to prepare bromoiododerivatives to obtain good selectivities.

Synthesis of novel halopyridinylboronic acids and esters. Part 1: 6-Halopyridin-3-yl-boronic acids and esters

This paper describes a general method for the synthesis and isolation of novel 6-halo-pyridin-3-yl-boronic acids and esters 2-5. These compounds are prepared taking in account a regioselective halogen-metal exchange with a trialkylborate starting from 2,5-dihalopyridines. All substrates studied to date provided a single regioisomeric boronic acid or ester product. Additionally, these compounds have been found to undergo Pd-catalysed coupling with a range of arylhalides and authorise a strategy to produce new pyridines libraries.

Functionalized pyridylboronic acids and their Suzuki cross-coupling reactions to yield novel heteroarylpyridines

2-Bromo-5-pyridylboronic acid 2a, 2-chloro-5-pyridylboronic acid 2b, 2-methoxy-5-pyridylboronic acid 2c, and 5-chloro-2-methoxy-4-pyridylboronic acid 4 have been synthesized and shown to undergo palladium-catalyzed cross-coupling reactions with heteroaryl bromides to yield novel heteroarylpyridine derivatives. The X-ray crystal structures of 2a and 2b have been obtained.