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(6-Methoxypyridin-3-yl)boronic acid (CAS 163105-89-3), also known as 6-methoxypyridine-3-boronic acid, is a heteroaromatic organoboron compound containing a boronic acid group at the 3-position and a methoxy group at the 6-position of a pyridine ring. Its structure combines the synthetic versatility of a boronic acid with the electronic characteristics of a nitrogen-containing aromatic heterocycle. The boronic acid functionality enables carbon–carbon bond formation, while the methoxy substituent influences the electronic properties and reactivity of the pyridine ring. These features make the compound a useful building block for medicinal chemistry, pharmaceutical intermediate synthesis, heterocyclic chemistry, and specialty organic synthesis.
Chemical Identifiers
| InChI | 1S/C6H8BNO3/c1-11-6-3-2-5(4-8-6)7(9)10/h2-4,9-10H,1H3 |
| InChI Key | DHADXDMPEUWEAS-UHFFFAOYSA-N |
| Smiles | OB(C1=CN=C(OC)C=C1)O |
| EC No. | 672-299-1 |
| MDL No. | MFCD02093044 |
| PubChem CID | 2734368 |
Applications
Applications in Suzuki–Miyaura Cross-Coupling Reactions
(6-Methoxypyridin-3-yl)boronic acid is useful in Suzuki–Miyaura cross-coupling reactions for preparing substituted pyridine derivatives. Under optimized palladium-catalyzed conditions, the boronic acid group can react with compatible aryl or heteroaryl halides to form new carbon–carbon bonds. This transformation enables the introduction of a 6-methoxypyridin-3-yl fragment into more complex molecular structures. Reaction conditions may require optimization because the pyridine nitrogen can interact with transition-metal catalysts, and heteroarylboronic acids may undergo competing protodeboronation under certain conditions.
Applications in Medicinal Chemistry
In medicinal chemistry, this compound serves as a building block for preparing methoxy-substituted pyridine research molecules. Pyridine rings are widely incorporated into pharmaceutical research compounds because their nitrogen atoms can influence molecular polarity, hydrogen-bonding interactions, and physicochemical properties. The methoxy group provides additional electronic modification and may affect interactions with biological targets. Through suitable cross-coupling reactions, researchers can introduce this substituted pyridine fragment into candidate compounds for lead optimization, analog synthesis, and structure–activity relationship studies.
Applications in Pharmaceutical Intermediate Synthesis
(6-Methoxypyridin-3-yl)boronic acid may support pharmaceutical intermediate synthesis requiring substituted nitrogen-containing aromatic structures. The boronic acid group provides a route for connecting the methoxypyridine fragment to suitable aromatic or heteroaromatic partners. The resulting intermediates may undergo further chemical transformations depending on the target molecular structure. Under appropriately selected conditions, the methoxy substituent may also be converted into a corresponding pyridone-related functionality, providing additional opportunities for molecular modification.
Applications in Heterocyclic Compound Synthesis
This compound is particularly useful in the preparation of linked heteroaromatic structures. Its boronic acid functionality enables coupling with suitable heteroaryl halides, allowing the construction of compounds containing pyridine and additional nitrogen-, oxygen-, or sulfur-containing heterocycles. Such transformations provide access to structurally diverse heterobiaryl molecules. Researchers may use these intermediates in molecular library development and the preparation of complex heterocyclic compounds for chemical and biological evaluation.
