N-Pyridin-2-yl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzamide Manufacturer CAS No.: 1383385-64-5

• Pyridine Ring: A six-membered ring containing one nitrogen atom, attached to the benzamide moiety at the 2-position.
• Benzamide Group: A benzene ring with an amide group, providing a rigid and planar structure that often facilitates interactions in synthetic processes.
• Dioxaborolane Ring: A five-membered cyclic ester of boronic acid, characterized by its stability and reactivity, with four methyl groups contributing to its steric bulk and stability.

Key Functional Groups

1. Pyridin-2-yl Group:
   • Contributes to the electron-rich nature of the molecule.
   • Can engage in coordination chemistry and other interactions.
2. Benzamide Core:
   • Provides a planar, stable framework.
   • Can participate in hydrogen bonding due to the amide group.
3. Tetramethyl Dioxaborolane:
   • Known for its use in forming stable boron-oxygen bonds.
   • Facilitates the molecule’s role as a boron donor in various chemical reactions, particularly the Suzuki-Miyaura coupling.

Applications

N-Pyridin-2-yl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzamide is primarily utilized in:

1. Suzuki-Miyaura Cross-Coupling Reactions:
   • This compound is a valuable reagent in these reactions, which are essential for forming carbon-carbon bonds.
   • It reacts with aryl or vinyl halides to produce biaryl or alkenyl derivatives, pivotal in constructing complex organic molecules.
2. Synthesis of Pharmaceuticals:
   • The compound’s ability to facilitate the formation of biaryl structures makes it instrumental in drug development.
   • Many pharmaceuticals, especially those targeting kinases or other protein functions, contain biaryl motifs.
3. Development of Organic Materials:
   • Used in the synthesis of organic semiconductors and polymers.
   • The robust and planar structure aids in the development of materials with desirable electronic properties.
4. Research in Medicinal Chemistry:
   • The boron-containing group in this compound can form unique interactions with biomolecules.
   • Explored as a building block in the design of new therapeutic agents due to its versatile reactivity.

Advantages in Synthetic Chemistry

1. Stability and Reactivity:
   • The boronate ester group is stable yet reactive under the right conditions, providing a balance that is highly desirable in synthesis.
   • The tetramethyl dioxaborolane group is particularly stable, preventing premature decomposition.
2. Functional Group Tolerance:
   • This compound can be used in reactions with a wide range of functional groups without interference.
   • Its ability to participate in reactions without altering sensitive functional groups makes it a versatile tool.
3. Ease of Handling:
   • Solid at room temperature, making it easy to handle and store.
   • Soluble in various organic solvents, facilitating its use in different synthetic protocols.

Conclusion

N-Pyridin-2-yl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzamide is a crucial reagent in modern organic synthesis. Its utility in the Suzuki-Miyaura cross-coupling reactions has made it indispensable for constructing complex molecular architectures, especially in the pharmaceutical and materials science sectors. The integration of a stable boronate ester with functionalized aromatic systems underscores its importance and versatility in synthetic chemistry.