Production Method 1

14529-53-4

854373-97-0

Reaction Conditions

1.1 Reagents: Lithium diisopropylamide Solvents: Tetrahydrofuran ,  Hexane ;  -50 °C; 1 h, -50 °C
1.2 Reagents: (T-4)-Hydrotris(2-propanolato)borate(1-) ;  -50 °C; 1 h, -50 °C; -50 °C → -10 °C
1.3 Reagents: Water

Reference

2-Ethoxy-3-pyridylboronic acid: a versatile reagent for the synthesis of highly-functionalized 3-aryl/heteroaryl-pyridines via Suzuki cross-coupling reactions

Thompson, Amy E.; et al, Tetrahedron, 2005, 61(21), 5131-5135

2-Ethoxypyridine-3-boronic acid Raw materials

• 2-Ethoxypyridine

2-Ethoxypyridine-3-boronic acid Preparation Products

• 2-Ethoxypyridine-3-boronic acid (854373-97-0)

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• Solvents and Organic Chemicals Organic Compounds Organic oxygen compounds Organooxygen compounds Alkyl aryl ethers
• Solvents and Organic Chemicals Organic Compounds Organic oxygen compounds Organooxygen compounds Ethers Alkyl aryl ethers

Introduction to 2-Ethoxypyridine-3-boronic acid (CAS No. 854373-97-0)

2-Ethoxypyridine-3-boronic acid, identified by the Chemical Abstracts Service Number (CAS No.) 854373-97-0, is a specialized organoboron compound that has garnered significant attention in the field of pharmaceutical and materials chemistry. This compound belongs to the pyridine derivative class, characterized by a pyridine ring substituted with an ethoxy group at the 2-position and a boronic acid functional group at the 3-position. The unique structural features of 2-Ethoxypyridine-3-boronic acid make it a valuable intermediate in organic synthesis, particularly in cross-coupling reactions such as the Suzuki-Miyaura coupling, which is widely employed in the construction of complex molecular architectures.

The boronic acid moiety in 2-Ethoxypyridine-3-boronic acid is highly reactive and participates in various catalytic processes, making it indispensable in the synthesis of fine chemicals and pharmaceuticals. Its ability to undergo palladium-catalyzed coupling reactions with aryl halides or heteroaryl halides has opened up numerous possibilities for constructing biaryl and biheteraryl systems, which are prevalent in biologically active molecules. The ethoxy group at the 2-position of the pyridine ring not only influences the electronic properties of the boronic acid but also modulates its solubility and reactivity, making it a versatile building block for medicinal chemists.

In recent years, 2-Ethoxypyridine-3-boronic acid has been extensively studied for its applications in drug discovery and development. The pyridine scaffold is a common motif in many drugs due to its ability to interact with biological targets through hydrogen bonding and hydrophobic interactions. The introduction of a boronic acid group at the 3-position allows for further functionalization, enabling the synthesis of novel compounds with tailored biological activities. For instance, researchers have explored its utility in generating kinase inhibitors, which are crucial in treating cancers and inflammatory diseases. The boronate ester linkage formed during Suzuki-Miyaura couplings provides a stable handle for further chemical manipulation, facilitating the development of prodrugs or conjugates that enhance drug delivery systems.

The synthesis of 2-Ethoxypyridine-3-boronic acid typically involves multi-step organic transformations starting from commercially available pyridine derivatives. Advanced synthetic methodologies have been developed to optimize yield and purity, ensuring that the final product meets the stringent requirements of pharmaceutical applications. Recent advances in transition metal catalysis have further refined these processes, enabling more efficient and scalable production methods. For example, palladium-catalyzed borylation reactions have been refined to achieve high selectivity and minimal side reactions, making them ideal for industrial-scale synthesis.

One of the most compelling applications of 2-Ethoxypyridine-3-boronic acid is in the field of materials science, particularly in organic electronics. The compound's ability to form stable polymers through cross-coupling reactions has led to the development of new conductive materials and optoelectronic devices. These materials are finding applications in flexible electronics, solar cells, and light-emitting diodes (LEDs), where their unique electronic properties offer advantages over traditional semiconductors. The boronic acid functionality also allows for post-polymerization modifications, enabling tunable material properties for specific applications.

The pharmaceutical industry has also leveraged 2-Ethoxypyridine-3-boronic acid for developing targeted therapies. By incorporating this compound into drug candidates, researchers can enhance binding affinity to therapeutic targets such as enzymes and receptors. For example, studies have demonstrated its role in synthesizing small-molecule inhibitors that disrupt pathogenic pathways involved in diseases like diabetes and neurodegenerative disorders. The boronic acid group's ability to form reversible covalent bonds with biological targets provides a unique mechanism for drug action, often leading to improved efficacy and reduced side effects.

Recent research has also highlighted the potential of 2-Ethoxypyridine-3-boronic acid in developing next-generation therapeutics such as antibody-drug conjugates (ADCs). The boronic acid moiety can be used as a linker between an antibody and a cytotoxic payload, ensuring targeted delivery to cancer cells while minimizing systemic toxicity. This approach has shown promise in clinical trials for treating various malignancies, underscoring the importance of organoboron compounds like 2-Ethoxypyridine-3-boronic acid in modern medicine.

The environmental impact of using 2-Ethoxypyridine-3-boronic acid has also been carefully evaluated. As part of sustainable chemistry initiatives, researchers are exploring greener synthetic routes that minimize waste and reduce energy consumption. Catalytic processes that employ recyclable catalysts or operate under mild conditions are being prioritized to align with global efforts toward environmental stewardship. Additionally, efforts are underway to develop biodegradable derivatives of this compound that can be safely disposed of without causing ecological harm.

In conclusion,2-Ethoxypyridine-3-boronic acid (CAS No. 854373-97-0) is a multifaceted compound with broad applications across pharmaceuticals, materials science, and organic electronics. Its unique structural features enable diverse chemical transformations, making it an indispensable tool for synthetic chemists. As research continues to uncover new uses for this compound,2-Ethoxypyridine-3-boronic acid is poised to play an increasingly significant role in advancing scientific innovation and technological development.

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