Production Method 1

944401-56-3

73183-34-3

1045861-32-2

944401-57-4

Reaction Conditions

1.1 Reagents: Potassium acetate Catalysts: Dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane addu… Solvents: 1,4-Dioxane ;  8 h, 115 °C; 115 °C → rt

Reference

Pyridine derivatives as PI3K inhibitors and their preparation, pharmaceutical compositions and use in the treatment of diseases

, World Intellectual Property Organization, , ,

(6-Amino-4-(trifluoromethyl)pyridin-3-yl)boronic acid Raw materials

• 5-Bromo-4-(trifluoromethyl)pyridin-2-amine
• Bis(pinacolato)diborane

(6-Amino-4-(trifluoromethyl)pyridin-3-yl)boronic acid Preparation Products

• 5-(tetramethyl-1,3,2-dioxaborolan-2-yl)-4-(trifluoromethyl)pyridin-2-amine (944401-57-4)
• (6-Amino-4-(trifluoromethyl)pyridin-3-yl)boronic acid (1045861-32-2)

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• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Pyridines and derivatives Aminopyridines and derivatives

Introduction to (6-Amino-4-(trifluoromethyl)pyridin-3-yl)boronic Acid (CAS No. 1045861-32-2)

(6-Amino-4-(trifluoromethyl)pyridin-3-yl)boronic acid is a specialized chemical compound with the CAS number 1045861-32-2. This compound has garnered significant attention in the field of pharmaceutical research due to its unique structural properties and potential applications in drug development. The presence of both amino and boronic acid functional groups makes it a versatile intermediate in organic synthesis, particularly in Suzuki-Miyaura cross-coupling reactions, which are widely employed in the construction of complex molecular architectures.

The compound's structure consists of a pyridine core substituted with an amino group at the 6-position and a trifluoromethyl group at the 4-position, further functionalized with a boronic acid moiety at the 3-position. This specific arrangement imparts distinct electronic and steric properties, making it an attractive candidate for various synthetic transformations. The trifluoromethyl group, in particular, is known for its ability to enhance metabolic stability and binding affinity in drug candidates, a critical factor in pharmaceutical design.

In recent years, there has been a surge in research focused on developing novel boronic acid derivatives for their applications in medicinal chemistry. Boronic acids are particularly valuable due to their role as key intermediates in the synthesis of biologically active compounds. The (6-amino-4-(trifluoromethyl)pyridin-3-yl)boronic acid derivative has been explored in several studies for its potential use in the synthesis of small-molecule inhibitors targeting various biological pathways.

One of the most notable applications of this compound is its use in the development of kinase inhibitors. Kinases are enzymes that play a crucial role in many cellular processes, and their dysregulation is often associated with diseases such as cancer. By leveraging the Suzuki-Miyaura cross-coupling reaction, researchers have been able to incorporate this boronic acid derivative into larger molecular frameworks designed to selectively inhibit specific kinases. This approach has led to the discovery of several promising lead compounds that are currently undergoing further investigation.

The trifluoromethyl group in the (6-amino-4-(trifluoromethyl)pyridin-3-yl)boronic acid derivative also contributes to its potential as a pharmacophore. This group can influence the electronic properties of adjacent functional groups, thereby affecting the overall binding characteristics of a drug molecule. Studies have shown that compounds containing trifluoromethyl groups often exhibit improved pharmacokinetic profiles, including enhanced solubility and bioavailability.

Furthermore, the amino group at the 6-position provides a site for further functionalization, allowing for the attachment of additional moieties that can modulate biological activity. This flexibility makes (6-amino-4-(trifluoromethyl)pyridin-3-yl)boronic acid a valuable building block in medicinal chemistry. Researchers have utilized this compound to synthesize libraries of derivatives, employing high-throughput screening methods to identify novel therapeutic agents.

Recent advances in computational chemistry have also facilitated the design and optimization of molecules incorporating this boronic acid derivative. Molecular modeling techniques allow researchers to predict the binding interactions between (6-amino-4-(trifluoromethyl)pyridin-3-yl)boronic acid and target proteins with high precision. This has enabled the rational design of more effective drug candidates, reducing the time and cost associated with traditional trial-and-error approaches.

The synthesis of (6-amino-4-(trifluoromethyl)pyridin-3-yl)boronic acid itself presents unique challenges due to its complex structure. However, recent methodologies have improved the efficiency and scalability of its production. For instance, transition-metal-catalyzed reactions have been optimized to achieve high yields of this intermediate under mild conditions. These advancements have made it more feasible for pharmaceutical companies to incorporate this compound into their drug discovery pipelines.

In conclusion, (6-amino-4-(trifluoromethyl)pyridin-3-yl)boronic acid (CAS No. 1045861-32-2) is a highly versatile compound with significant potential in pharmaceutical research. Its unique structural features make it an excellent candidate for synthesizing novel drug candidates targeting various diseases. As research continues to evolve, it is likely that this compound will play an increasingly important role in the development of next-generation therapeutics.

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