Production Method 1

1000340-39-5

918515-16-9

Reaction Conditions

1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ;  rt → -78 °C; 30 min, -78 °C
1.2 -78 °C → 25 °C; 2 h, 25 °C
1.3 Reagents: Water

Reference

Amine derivatives useful as anticancer agents and their preparation, pharmaceutical compositions and use in the treatment of neoplasm

, World Intellectual Property Organization, , ,

Production Method 2

55052-28-3

918515-16-9

Reaction Conditions

1.1 Reagents: Acetic acid Solvents: Water ;  overnight, 100 °C
1.2 Reagents: Water ;  > 1 min, cooled

Reference

Preparation of triazadibenzo[cd,f]azulene compounds as CDK9 kinase inhibitors for treatment of cancer

, United States, , ,

Production Method 3

55052-28-3

918515-16-9

Reaction Conditions

1.1 Reagents: Acetic acid Solvents: Water ;  14 h, rt → reflux; reflux → rt

Reference

Preparation of pyrimidinylindolecarboxamide derivatives and analogs for use as P2X7 receptor modulators

, World Intellectual Property Organization, , ,

Production Method 4

55052-28-3

918515-16-9

Reaction Conditions

1.1 Catalysts: Acetic acid Solvents: Water ;  rt → reflux; 1.5 h, reflux; reflux → 25 °C

Reference

New 5-[(1H-pyrrolo[2,3-b]pyridin-3-yl)methylene]substituted imidazolone derivatives, their preparation and their pharmaceutical use as inhibitors of protein kinases, particularly CDC7, and antiproliferative agents

, France, , ,

Production Method 5

55052-28-3

918515-16-9

Reaction Conditions

1.1 Solvents: Acetic acid ,  Water ;  12 h, 120 °C

Reference

Nature-inspired remodeling of (aza)indoles to meta-aminoaryl nicotinates for late-stage conjugation of vitamin B3 to (hetero)arylamines

Varun, Begur Vasanthkumar ; Vaithegi, Kannan ; Yi, Sihyeong ; Park, Seung Bum, Nature Communications, 2020, 11(1),

Production Method 6

55052-28-3

918515-16-9

Reaction Conditions

1.1 Solvents: Acetic acid ,  Water ;  18 h, rt → 100 °C

Reference

Preparation of pyrrolo[2,3-b]pyridine compounds as MRCK inhibitors for treatment of cancer

, World Intellectual Property Organization, , ,

Production Method 7

55052-28-3

918515-16-9

Reaction Conditions

1.1 Solvents: Acetic acid ,  Water ;  14 h, rt → reflux; reflux → rt

Reference

Preparation of heteroaryl amide analogs as P2X7 receptor modulators

, World Intellectual Property Organization, , ,

Production Method 8

918515-16-9

Reaction Conditions

Reference

Pyrrolo[2,3-b]pyridine derivatives as protein kinase inhibitors and their preparation, pharmaceutical compositions and use in the treatment of diseases

, World Intellectual Property Organization, , ,

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

• 3-Bromo-4-chloro-1H-pyrrolo[2,3-b]pyridine
• 4-Chloro-1H-pyrrolo[2,3-b]pyridine

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

• 4-Chloro-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde (918515-16-9)

• 1. Enabling shape memory and healable effects in a conjugated polymer by incorporating siloxane via dynamic imine bond?
  Yaling Zhang,Chunhui Dai,Shiwei Zhou,Bin Liu Chem. Commun., 2018,54, 10092-10095
• 2. Emergence of microfluidic wearable technologies
  Joo Chuan Yeo,Kenry Lab Chip, 2016,16, 4082-4090
• 3. Evidence of rutile-to-anatase photo-induced electron transfer in mixed-phase TiO2 by solid-state NMR spectroscopy?
  Weili Dai,Guangjun Wu,Michael Hunger Chem. Commun., 2015,51, 13779-13782
• 4. Excimer–monomer switch: a reaction-based approach for selective detection of fluoride?
  Qiao Song,Angela Bamesberger,Lingyun Yang,Haley Houtwed,Haishi Cao Analyst, 2014,139, 3588-3592
• 5. Dissociation of aryl sulfonyl phthalimide radical anions: relevance to the biological activity of arylsulfonyl amides?
  Abdelaziz Houmam,Emad M. Hamed Chem. Commun., 2012,48, 11328-11330

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

Introduction to 4-Chloro-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde (CAS No. 918515-16-9)

4-Chloro-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde (CAS No. 918515-16-9) is a highly versatile heterocyclic compound that has garnered significant attention in the field of pharmaceutical chemistry and medicinal research. This compound belongs to the pyrrolopyridine class, a scaffold that is widely recognized for its broad biological activity and potential therapeutic applications. The presence of both a chloro substituent and an aldehyde functional group makes it a valuable intermediate in the synthesis of more complex molecules, particularly in the development of novel drug candidates.

The pyrrolo[2,3-b]pyridine core is a privileged structure in drug discovery, exhibiting a wide range of pharmacological properties due to its ability to interact with various biological targets. The introduction of a chloro group at the 4-position and an aldehyde group at the 3-position enhances its reactivity, making it an ideal building block for further functionalization. This compound has been extensively studied in recent years for its role in the synthesis of small-molecule inhibitors targeting key enzymes and receptors involved in diseases such as cancer, inflammation, and neurodegeneration.

Recent advancements in medicinal chemistry have highlighted the importance of 4-Chloro-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde as a key intermediate in the development of next-generation therapeutics. For instance, researchers have utilized this compound to synthesize novel inhibitors of kinases, which are critical targets in oncology. The aldehyde group provides a convenient handle for further derivatization via condensation reactions, allowing for the creation of diverse pharmacophores. Additionally, the chloro substituent can participate in metal-catalyzed cross-coupling reactions, enabling the introduction of additional functional groups with high precision.

In the context of oncology research, 4-Chloro-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde has been employed in the design of small-molecule inhibitors targeting tyrosine kinases and other signaling proteins involved in tumor growth and progression. These inhibitors often require precise structural features to achieve high affinity and selectivity. The pyrrolopyridine scaffold provides a suitable platform for modulating binding interactions with biological targets, while the aldehyde and chloro groups offer opportunities for further chemical manipulation to optimize potency and reduce off-target effects.

Moreover, the compound has shown promise in preclinical studies as a precursor for synthesizing molecules with anti-inflammatory properties. Inflammation is a hallmark of numerous chronic diseases, including rheumatoid arthritis and atherosclerosis. By leveraging the reactivity of 4-Chloro-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde, chemists have been able to develop novel agents that interfere with key inflammatory pathways. The ability to fine-tune the structure through subsequent chemical modifications has allowed for the identification of compounds with improved pharmacokinetic profiles and reduced toxicity.

The synthesis of 4-Chloro-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde typically involves multi-step organic transformations starting from readily available precursors. Common synthetic routes include cyclization reactions followed by functional group interconversions to introduce the desired substituents. The use of palladium-catalyzed cross-coupling reactions has been particularly effective in constructing the pyrrolopyridine core with high yields and regioselectivity. These synthetic strategies highlight the compound's synthetic utility and its potential as a cornerstone in medicinal chemistry.

Recent studies have also explored the use of 4-Chloro-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde in combinatorial chemistry approaches to discover novel drug candidates. By generating libraries of derivatives through automated parallel synthesis techniques, researchers can rapidly screen large collections of compounds for biological activity. This approach has been successful in identifying lead structures with promising therapeutic profiles that would be difficult to uncover using traditional one-compound-at-a-time methods.

The versatility of 4-Chloro-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde extends beyond its role as an intermediate; it also serves as a model system for understanding structure-activity relationships (SAR) within the pyrrolopyridine class. By systematically varying substituents on this scaffold, researchers can gain insights into how different structural features influence biological activity. These insights are crucial for designing more effective drugs with improved efficacy and safety profiles.

In conclusion,4-Chloro-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde (CAS No. 918515-16-9) is a multifaceted compound with significant potential in pharmaceutical research and drug development. Its unique structural features make it an invaluable tool for synthesizing novel therapeutics targeting various diseases. As our understanding of biological pathways continues to evolve, compounds like this will play an increasingly important role in discovering next-generation medicines that address unmet medical needs.

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