6-Chloro-1H-pyrazolo[3,4-b]pyridine

This compound is typically isolated as a crystalline solid ranging from white to off-white in appearance. Its molecular formula is C6H4ClN3, corresponding to a molecular weight of 153.57. The melting point generally falls within the range of 210–215 ℃, often with decomposition observed upon prolonged heating. The calculated density is approximately 1.57 g/cm³ under ambient conditions. It exhibits limited solubility in common organic solvents such as dichloromethane and methanol, but dissolves more readily in polar aprotic solvents like dimethyl sulfoxide and dimethylformamide. The compound is sparingly soluble in water and practically insoluble in non-polar solvents such as hexane. The molecule contains a fused pyrazolo[3,4-b]pyridine core with a chlorine atom at the 6-position. The pyrazole NH is acidic and can participate in hydrogen bonding, while the chlorine is activated toward nucleophilic aromatic substitution by the electron-withdrawing ring nitrogen atoms. Storage in tightly sealed containers protected from light and moisture at ambient temperature is generally adequate, though desiccated conditions are recommended for prolonged storage. Contact with strong bases, strong nucleophiles, and strong oxidizing agents should be avoided.

6-Chloro-1H-pyrazolo[3,4-b]pyridine is a fused heteroaromatic compound belonging to the pyrazolopyridine family, featuring a pyrazole ring fused to a pyridine ring in a [3,4-b] orientation. This nitrogen-rich scaffold provides multiple hydrogen bond accepting sites through the ring nitrogen atoms and a hydrogen bond donor via the pyrazole NH, enabling specific interactions with biological targets such as kinase ATP-binding pockets. The chlorine atom at the 6-position is activated toward nucleophilic substitution and transition-metal-catalyzed cross-coupling reactions due to the electron-withdrawing effects of the adjacent ring nitrogens. The rigid, planar architecture imposes conformational constraint, which can enhance binding selectivity and metabolic stability in drug candidates. This compact, functionalized heterocycle serves as a valuable building block in medicinal chemistry for constructing kinase inhibitors and other therapeutic agents, where the pyrazolopyridine core can mimic the adenine portion of ATP and engage in key hydrogen bonding interactions with hinge region residues.

In drug discovery, this chloropyrazolopyridine is extensively employed as a key building block for synthesizing kinase inhibitors targeting cancer and inflammatory diseases. The chlorine atom enables palladium-catalyzed cross-coupling reactions such as Suzuki, Sonogashira, and Buchwald-Hartwig couplings to introduce diverse aryl, heteroaryl, or amino groups. The pyrazolopyridine core can occupy ATP-binding pockets with high complementarity, forming critical hydrogen bonds through the NH and ring nitrogen with hinge region residues of kinases.

The compound serves as a precursor for constructing more complex fused heterocyclic systems through further annulation reactions. After functionalization at the chlorine position, the resulting substituents can participate in intramolecular cyclization to access tetracyclic architectures with enhanced pharmacological properties. These ring systems are investigated for their potential as selective kinase inhibitors and as probes for studying signal transduction pathways.

In crop protection chemistry, this scaffold is utilized for developing novel fungicides and herbicides. Pyrazolopyridine derivatives are known to interfere with key enzymes in plant pathogens and pests, including succinate dehydrogenase in fungi. The chlorine atom allows fine-tuning of lipophilicity and electronic properties to optimize target affinity and environmental persistence, while the rigid heterocyclic core ensures specific binding to active sites.

As a versatile synthetic intermediate, 6-chloro-1H-pyrazolo[3,4-b]pyridine participates in diverse transformations including nucleophilic aromatic substitution, palladium-catalyzed cross-couplings, and directed metalation reactions. The pyrazole NH can be protected, alkylated, or acylated to further elaborate the scaffold. Its utility extends to the synthesis of functional materials and molecular probes where the pyrazolopyridine core imparts desirable electronic and structural properties, such as metal coordination and fluorescence.

Popularni tagovi: 6-chloro-1h-pyrazolo[3,4-b]pyridine, China 6-chloro-1h-pyrazolo[3,4-b]pyridine manufacturers, suppliers, 15069-92-8, 2 Nitropiridin 5 karboksilna kiselina, 4-Izopropilpiridin, 525-76-8, C1 CC NC C1C OONOO, O=C(O)C1=NC=C(O)C=C1