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4-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (CAS 1171891-31-8) is a heteroaromatic boronic acid pinacol ester featuring a methyl group at the 4-position and a pinacol boronate group at the 3-position of the pyridine ring. This compound is a useful building block for organic synthesis, medicinal chemistry, pharmaceutical intermediate development, and specialty chemical research. The pyridine ring introduces a nitrogen-containing aromatic framework, while the boronic ester functionality provides a convenient site for carbon–carbon bond formation through suitable cross-coupling reactions. Its defined substitution pattern makes it valuable for preparing structurally diverse heteroaromatic compounds.
Chemical Identifiers
| InChI | InChI=1S/C12H18BNO2/c1-9-6-7-14-8-10(9)13-15-11(2,3)12(4,5)16-13/h6-8H,1-5H3 |
| InChI Key | GZYZXNXJTPRMKF-UHFFFAOYSA-N |
| Smiles | CC1(C)C(C)(C)OB(C2=C(C)C=CN=C2)O1 |
| EC No. | 830-462-6 |
| MDL No. | MFCD12923382 |
| PubChem CID | 57370080 |
Applications
Applications in Suzuki–Miyaura Cross-Coupling Reactions
4-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine can be used in Suzuki–Miyaura cross-coupling reactions to construct substituted pyridine derivatives and other heteroaryl-containing structures. Under appropriate palladium-catalyzed conditions, the pinacol boronate functionality can react with compatible aryl or heteroaryl halides and pseudohalides to form new carbon–carbon bonds. This enables the introduction of a 4-methylpyridin-3-yl fragment into more complex molecular frameworks. Reaction optimization may be necessary because heteroaromatic nitrogen atoms and substrate substitution patterns can influence catalytic performance.
Applications in Medicinal Chemistry
In medicinal chemistry, this compound serves as a building block for preparing nitrogen-containing heteroaromatic compounds and exploring structure–activity relationships. Pyridine rings are frequently incorporated into research molecules because their nitrogen atoms can influence molecular polarity, hydrogen-bonding interactions, and physicochemical properties. The methyl substituent provides an additional structural feature that may affect steric characteristics and molecular recognition. Researchers can use this compound in lead optimization, analog synthesis, and molecular library development to investigate the effects of substituted pyridine fragments on candidate molecules.
Applications in Pharmaceutical Intermediate Synthesis
4-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine may support pharmaceutical research programs requiring substituted pyridine intermediates. Its boronic ester functionality allows the 4-methylpyridin-3-yl group to be incorporated into suitable target structures through compatible coupling reactions. This approach can simplify access to complex heteroaromatic frameworks and support multistep synthesis strategies. The compound is particularly relevant to research projects involving the preparation of structurally defined nitrogen-containing intermediates.
Applications in Specialty Organic Synthesis
Beyond pharmaceutical research, 4-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine can serve as an intermediate in specialty organic synthesis. The pinacol boronate group offers a convenient organoboron functionality for selected carbon–carbon bond-forming reactions, while the substituted pyridine ring contributes a defined heteroaromatic structural unit. It may support the synthesis of advanced organic intermediates and functional molecules, depending on the target structure and selected reaction conditions.
