Production Method 1

626-60-8

73183-34-3

865186-94-3

Reaction Conditions

1.1 Catalysts: Di-μ-chlorobis[(1,2,5,6-η)-1,5-cyclooctadiene]diiridium ,  2642090-87-5 Solvents: p-Xylene ,  Dodecane ;  30 h, rt
1.2 24 h, 80 °C

Reference

Enzyme-like Supramolecular Iridium Catalysis Enabling C-H Bond Borylation of Pyridines with meta-Selectivity

Trouve, Jonathan; et al, Angewandte Chemie, 2021, 60(33), 18006-18013

3-Chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine Raw materials

• 3-Chloropyridine
• Bis(pinacolato)diborane

3-Chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine Preparation Products

• 3-Chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (865186-94-3)

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• Other Chemical Reagents Derivatization Reagents
• Solvents and Organic Chemicals Organic Compounds Acids/Esters
• Solvents and Organic Chemicals Organic Compounds Alcohol/Ether

Research Briefing on 3-Chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (CAS: 865186-94-3)

3-Chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (CAS: 865186-94-3) is a boronic ester derivative that has garnered significant attention in the field of medicinal chemistry and drug discovery. This compound serves as a key intermediate in the synthesis of various biologically active molecules, particularly in the development of kinase inhibitors and other targeted therapies. Recent studies have highlighted its utility in Suzuki-Miyaura cross-coupling reactions, which are pivotal for constructing complex heterocyclic scaffolds found in many pharmaceutical agents.

Recent research has focused on optimizing the synthetic routes for 3-Chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine to improve yield and purity. A 2023 study published in the Journal of Medicinal Chemistry demonstrated a novel catalytic system that enhances the efficiency of boron incorporation into the pyridine ring, reducing byproduct formation. This advancement is critical for scaling up production while maintaining cost-effectiveness, a key consideration for industrial applications.

In addition to its synthetic applications, 3-Chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine has been investigated as a building block for PROTACs (Proteolysis Targeting Chimeras). A recent preprint on bioRxiv detailed its incorporation into a new class of EGFR-targeting PROTACs, showing promising results in overcoming resistance mutations in non-small cell lung cancer models. The boronic ester moiety was found to be essential for maintaining the compound's stability in physiological conditions while allowing for efficient target protein degradation.

Structural-activity relationship (SAR) studies involving this compound have revealed interesting insights into the importance of the chlorine substituent at the 3-position. Research published in ACS Medicinal Chemistry Letters (2024) demonstrated that this specific substitution pattern significantly influences the binding affinity to certain protein kinases, particularly those in the CDK family. These findings open new avenues for designing more selective kinase inhibitors with improved therapeutic windows.

From a safety and toxicological perspective, recent investigations have addressed the compound's metabolic stability and potential off-target effects. A 2024 study in Chemical Research in Toxicology reported that the dioxaborolane ring shows remarkable stability against hepatic metabolism, while the pyridine ring undergoes predictable oxidation pathways. This metabolic profile makes it an attractive scaffold for further medicinal chemistry optimization.

Looking forward, the versatility of 3-Chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine continues to inspire innovative applications. Current research directions include its use in DNA-encoded library technology for high-throughput screening and as a precursor for novel PET imaging agents. The compound's unique combination of chemical stability and reactivity positions it as a valuable tool in both drug discovery and chemical biology research.

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