• 1. Regioselective deoxygenative chalcogenation of 7-azindole N-oxides promoted by I2/PEG-200
  Shanshan Liu,Heng Yang,Lin-Yu Jiao,Jian-Hua Zhang,Chen Zhao,Yangmin Ma,Xiufang Yang Org. Biomol. Chem. 2019 17 10073

Comprehensive Overview of 1H-Pyrrolo[2,3-b]pyridine-5-carbonitrile (CAS No. 517918-95-5)

1H-Pyrrolo[2,3-b]pyridine-5-carbonitrile (CAS No. 517918-95-5) is a heterocyclic organic compound that has garnered significant attention in pharmaceutical and agrochemical research due to its unique structural properties. This nitrogen-containing bicyclic scaffold is a key intermediate in the synthesis of bioactive molecules, particularly in the development of kinase inhibitors and other therapeutic agents. The compound's pyrrolopyridine core is structurally analogous to purine bases, making it a valuable building block in medicinal chemistry.

In recent years, the demand for 1H-Pyrrolo[2,3-b]pyridine derivatives has surged, driven by their applications in drug discovery. Researchers are particularly interested in its carbonitrile functional group, which offers versatile reactivity for further derivatization. The compound's CAS No. 517918-95-5 is frequently searched in scientific databases, reflecting its importance in the development of small-molecule drugs targeting cancer, inflammation, and central nervous system disorders.

The synthesis of 1H-Pyrrolo[2,3-b]pyridine-5-carbonitrile typically involves multi-step reactions, including cyclization and nitrile introduction. Its high purity and structural stability make it suitable for high-throughput screening and combinatorial chemistry. The compound's molecular weight (159.16 g/mol) and logP value (a key parameter in drug-likeness assessments) are often discussed in pharmacokinetic studies.

From an industrial perspective, 517918-95-5 is classified as a fine chemical, with strict quality control requirements for pharmaceutical-grade material. Its solubility profile (moderate in organic solvents like DMSO and methanol) is critical for formulation studies. Recent patent literature highlights its use in JAK/STAT signaling pathway inhibitors, aligning with the growing focus on immunomodulatory therapies.

Environmental and safety assessments of 1H-Pyrrolo[2,3-b]pyridine-5-carbonitrile indicate it requires standard laboratory handling procedures. While not classified as hazardous under GHS criteria, proper personal protective equipment (PPE) is recommended during manipulation. The compound's thermal stability data (typically stable below 200°C) is important for storage and transportation considerations.

Analytical characterization of CAS 517918-95-5 typically involves HPLC purity analysis, mass spectrometry, and NMR spectroscopy (with characteristic aromatic proton signals between 7.5-9.0 ppm). The UV-Vis spectrum shows strong absorption in the 250-300 nm range, which is valuable for detection method development. These analytical parameters are crucial for quality assurance in contract manufacturing organizations (CMOs).

Market trends show increasing interest in pyrrolopyridine-based compounds, with 517918-95-5 serving as a strategic intermediate. The global push for targeted cancer therapies has particularly driven demand, as this scaffold appears in several clinical-stage tyrosine kinase inhibitors. Its intellectual property landscape reveals multiple patent filings across major pharmaceutical jurisdictions.

Future research directions for 1H-Pyrrolo[2,3-b]pyridine-5-carbonitrile include exploration of its metal-catalyzed coupling reactions and applications in PROTAC technology (proteolysis targeting chimeras). The compound's structure-activity relationship (SAR) studies continue to provide insights for fragment-based drug design. These developments position CAS No. 517918-95-5 as a compound of enduring significance in biopharmaceutical innovation.

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