Production Method 1

651744-48-8

958230-19-8

Reaction Conditions

1.1 Reagents: sec-Butyllithium Solvents: Tetrahydrofuran ,  Cyclohexane ;  15 min, -78 °C; 1 h, -78 °C
1.2 -78 °C; 1 h, -78 °C
1.3 Reagents: Hydrochloric acid Solvents: 1,4-Dioxane
1.4 Reagents: Sodium bicarbonate Solvents: Water

Reference

Novel tricyclic compounds as SYK inhibitors and their preparation and use in the treatment of immune and oncological diseases

, World Intellectual Property Organization, , ,

4-Chloro-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde Raw materials

• 4-chloro-1-[tris(propan-2-yl)silyl]-1H-pyrrolo[2,3-b]pyridine

4-Chloro-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde Preparation Products

• 4-Chloro-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde (958230-19-8)

• 1. An intensified π-hole in beryllium-doped boron nitride meshes: its determinant role in CO2 conversion into hydrocarbon fuels?
  Luis Miguel Azofra,Douglas R. MacFarlane,Chenghua Sun Chem. Commun., 2016,52, 3548-3551
• 2. An intramolecular tryptophan-condensation approach for peptide stapling?
  Eunice Y.-L. Hui,Bhimsen Rout,Yaw Sing Tan,Kok-Ping Chan,Charles W. Johannes Org. Biomol. Chem., 2018,16, 389-392
• 3. An algal process treatment combined with the Fenton reaction for high concentrations of amoxicillin and cefradine
  Haitao Li,Yu Pan,Zhizhi Wang,Shan Chen,Ruixin Guo,Jianqiu Chen RSC Adv., 2015,5, 100775-100782
• 4. An artificial enzyme cascade amplification strategy for highly sensitive and specific detection of breast cancer-derived exosomes?
  Huiying Xu,Lu Zheng,Yu Zhou,Bang-Ce Ye Analyst, 2021,146, 5542-5549
• 5. An integrated cathode and solid electrolyte via in situ polymerization with significantly reduced interface resistance?
  Jialiang Yuan,Ran Dong,Yuan Li,Yang Liu,Zhuo Zheng,Yuxia Liu,Yan Sun,Benhe Zhong,Zhenguo Wu,Xiaodong Guo Chem. Commun., 2021,57, 13004-13007

• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Pyrrolopyridines Pyrrolopyridines
• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Pyrrolopyridines

4-Chloro-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde (CAS No. 958230-19-8): A Key Intermediate in Modern Pharmaceutical Research

4-Chloro-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde, with the chemical identifier CAS No. 958230-19-8, represents a significant compound in the realm of pharmaceutical chemistry. This heterocyclic aldehyde has garnered considerable attention due to its versatile structural framework and its role as a crucial intermediate in the synthesis of various biologically active molecules. The compound’s unique pyrrolopyridine core, combined with a reactive aldehyde group, makes it an invaluable building block for medicinal chemists exploring novel therapeutic agents.

The< strong>pyrrolo[2,3-b]pyridine scaffold is a privileged structure in drug discovery, frequently appearing in molecules with diverse pharmacological activities. Its aromatic system allows for interactions with multiple biological targets, including enzymes and receptors, making it a preferred motif in the design of small-molecule drugs. The presence of a< strong>chloro substituent at the 4-position enhances the electrophilicity of the ring, facilitating further functionalization through nucleophilic aromatic substitution or cross-coupling reactions. Additionally, the< strong>aldehyde functionality at the 5-position provides a reactive site for condensation reactions, enabling the construction of more complex structures.

In recent years, there has been a surge in research focused on developing treatments for neurological disorders, infectious diseases, and cancer. The< strong>4-Chloro-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde has emerged as a pivotal intermediate in several high-profile drug development programs. For instance, studies have demonstrated its utility in synthesizing novel kinase inhibitors targeting aberrant signaling pathways implicated in cancer progression. These inhibitors often rely on the pyrrolopyridine core to achieve high binding affinity and selectivity.

One notable application of this compound is in the synthesis of< strong>neuroprotective agents. Researchers have leveraged its structural features to develop molecules that modulate neurotransmitter systems involved in conditions such as Alzheimer’s disease and Parkinson’s disease. The aldehyde group serves as a key point for further derivatization, allowing chemists to introduce pharmacophores that interact with specific neurotransmitter receptors or enzymes. Preliminary findings suggest that certain derivatives exhibit promising neuroprotective effects in preclinical models.

The< strong>CAS No. 958230-19-8-labeled compound has also found relevance in addressing infectious diseases. The growing threat of antibiotic-resistant bacteria has prompted investigations into novel antimicrobial agents. The pyrrolopyridine scaffold has been incorporated into molecules designed to disrupt bacterial cell wall synthesis or interfere with essential metabolic pathways. The chloro and aldehyde substituents play critical roles in optimizing these interactions, enhancing both potency and selectivity against bacterial targets.

The versatility of< strong>4-Chloro-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde extends beyond its role as an intermediate; it also serves as a starting point for exploring new synthetic methodologies. Advances in catalytic chemistry have enabled innovative approaches to functionalize this scaffold, including transition-metal-catalyzed coupling reactions and organometallic transformations. These techniques have opened up new avenues for constructing complex heterocyclic systems with tailored biological properties.

The< strong>CAS registry number 958230-19-8 ensures traceability and consistency across different batches of this compound, which is essential for reproducible research outcomes. Quality control measures are stringent to guarantee purity and minimize impurities that could affect downstream applications. Manufacturers adhere to Good Manufacturing Practices (GMP) to ensure that the product meets the highest standards for pharmaceutical use.

In conclusion, the< strong>4-Chloro-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde stands as a cornerstone in modern pharmaceutical research due to its structural versatility and functional reactivity. Its applications span across multiple therapeutic areas, from oncology to neurology and infectious diseases, underscoring its importance as a building block for innovative drug discovery. As research continues to uncover new biological targets and synthetic strategies, this compound will undoubtedly remain at the forefront of medicinal chemistry innovation.

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