Production Method 1

685513-96-6

876343-81-6

Reaction Conditions

1.1 Reagents: Sulfuric acid Solvents: Isopropanol
1.2 Reagents: Sodium hydride Solvents: Tetrahydrofuran
1.3 -

Reference

Discovery of a novel azaindole class of antibacterial agents targeting the ATPase domains of DNA gyrase and Topoisomerase IV

Manchester, John I.; et al, Bioorganic & Medicinal Chemistry Letters, 2012, 22(15), 5150-5156

1-(benzenesulfonyl)-5-bromo-4-chloro-1H-pyrrolo[2,3-b]pyridine Raw materials

• 5-bromo-4-chloro-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine

1-(benzenesulfonyl)-5-bromo-4-chloro-1H-pyrrolo[2,3-b]pyridine Preparation Products

• 1-(benzenesulfonyl)-5-bromo-4-chloro-1H-pyrrolo[2,3-b]pyridine (876343-81-6)

• 1. Emerging investigators
  Polym. Chem., 2015,6, 5501-5502
• 2. Excimer formation effects and trap-assisted charge recombination loss channels in organic solar cells of perylene diimide dimer acceptors?
  Min Kim,Jae-Joon Lee,Tengling Ye,Panagiotis E. Keivanidis,Kilwon Cho J. Mater. Chem. C, 2020,8, 1686-1696
• 3. Evidence of field induced slow magnetic relaxation in cis-[Co(hfac)2(H2O)2] exhibiting tri-axial anisotropy with a negative axial component?
  Denis V. Korchagin,Elena A. Yureva,Alexander V. Akimov,Eugenii Ya. Misochko,Gennady V. Shilov,Artem D. Talantsev,Roman B. Morgunov,Alexander A. Shakin,Sergey M. Aldoshin,Boris S. Tsukerblat Dalton Trans., 2017,46, 7540-7548
• 4. Enabling chloride salts for thermal energy storage: implications of salt purity?
  J. Matthew Kurley,Phillip W. Halstenberg,Abbey McAlister,Stephen Raiman,Richard T. Mayes RSC Adv., 2019,9, 25602-25608
• 5. Examination of deposit in commercial diluted phosphoric acid
  Analyst, 1880,5, 146-147

Comprehensive Analysis of 1-(Benzenesulfonyl)-5-bromo-4-chloro-1H-pyrrolo[2,3-b]pyridine (CAS No. 876343-81-6)

The compound 1-(benzenesulfonyl)-5-bromo-4-chloro-1H-pyrrolo[2,3-b]pyridine (CAS No. 876343-81-6) is a highly specialized heterocyclic molecule that has garnered significant attention in pharmaceutical and agrochemical research. With its unique pyrrolopyridine core and functionalized substituents, this compound serves as a versatile building block for drug discovery and material science applications. The presence of both bromine and chlorine atoms at the 5- and 4-positions, respectively, enhances its reactivity, making it a valuable intermediate for cross-coupling reactions and further derivatization.

In recent years, the demand for pyrrolopyridine derivatives has surged due to their broad biological activities, including kinase inhibition and antimicrobial properties. Researchers are particularly interested in the benzenesulfonyl moiety of this compound, as it can influence pharmacokinetic properties such as solubility and metabolic stability. The CAS 876343-81-6 compound is frequently discussed in forums focusing on medicinal chemistry optimization and structure-activity relationship (SAR) studies, reflecting its relevance in modern drug design.

From a synthetic chemistry perspective, the 5-bromo-4-chloro substitution pattern offers strategic advantages for sequential functionalization. This aligns with current trends in late-stage diversification, a hot topic in organic synthesis that emphasizes efficiency and atom economy. Laboratories specializing in high-throughput screening often explore this compound’s potential as a scaffold for generating targeted libraries against diseases like cancer and inflammatory disorders.

Environmental and regulatory considerations are also critical when working with halogenated pyrrolopyridines. While the compound itself is not classified as hazardous, proper handling protocols are recommended due to its reactivity. The scientific community has shown growing interest in green chemistry alternatives for synthesizing such intermediates, with microwave-assisted and flow chemistry methods gaining traction as sustainable options.

Analytical characterization of 1-(benzenesulfonyl)-5-bromo-4-chloro-1H-pyrrolo[2,3-b]pyridine typically involves advanced techniques like NMR spectroscopy, HPLC-MS, and X-ray crystallography. These methods confirm the compound’s purity and structural integrity, which are essential for reproducibility in research. Patent literature reveals its incorporation in several biologically active molecules, particularly those targeting protein-protein interactions—a frontier area in therapeutic development.

Market-wise, suppliers of CAS 876343-81-6 cater to academic institutions and pharmaceutical companies engaged in fragment-based drug discovery. Pricing and availability fluctuate based on synthesis complexity and scale-up challenges, prompting discussions about cost-effective synthetic routes in industry publications. The compound’s chromatographic behavior and storage stability are additional practical concerns addressed in technical datasheets.

Emerging applications include its use in photoaffinity labeling probes for studying enzyme mechanisms, capitalizing on the aryl halide groups’ photoreactivity. This intersects with the rising popularity of chemical biology tools in proteomics research. Furthermore, computational chemists employ molecular docking simulations to predict how derivatives of this scaffold might interact with biological targets, leveraging AI-driven drug design platforms—a frequently searched topic in modern pharmacology.

In summary, 1-(benzenesulfonyl)-5-bromo-4-chloro-1H-pyrrolo[2,3-b]pyridine represents a multifaceted tool for innovators across chemical and life sciences. Its structural features continue to inspire novel research directions, from small-molecule therapeutics to functional materials, ensuring its enduring significance in scientific advancement.

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