640735-23-5 | 4-FLUORO-7-AZAINDOLE

CAS:640735-23-5 | 4-FLUORO-7-AZAINDOLE,Description

Synthesis Analysis

The synthesis of 4-Fluoro-7-azaindole and related compounds typically involves strategic functionalization of azaindoles or fluoropyridines. Nuhant et al. (2015) described a versatile synthesis route starting from substituted 2-fluoropyridines, utilizing C3-metalation and subsequent reactions to yield highly functionalized 7-azaindoles (Nuhant et al., 2015). Additionally, Caldwell et al. (2007) demonstrated the use of microwave heating for the nucleophilic aromatic substitution of 4-halo-7-azaindoles with cyclic secondary amines, highlighting the reactivity of 4-fluoro-7-azaindoles towards SNAr reactions under these conditions (Caldwell et al., 2007).

Molecular Structure Analysis

The molecular structure of 4-Fluoro-7-azaindole derivatives reveals interesting intermolecular interactions. Kumar et al. (2011) investigated the structure of a 7-azaindole···2-fluoropyridine dimer, showing the competition between N-H···N and N-H···F interactions through spectroscopic techniques and quantum chemistry calculations (Kumar et al., 2011) . These findings underscore the complex hydrogen bonding dynamics that can influence the structural characteristics of 4-Fluoro-7-azaindole complexes.

Chemical Reactions and Properties

The chemical reactivity of 4-Fluoro-7-azaindole involves engaging in various bond-forming reactions. Liu et al. (2014) presented rare instances of radical ipso-substitution of a carbon-fluorine bond, leading to highly functionalized 5,6-difluoro-7-azaindolines, demonstrating the synthetic utility of this approach in generating fluoro-7-azaindole derivatives (Liu et al., 2014).

Scientific Research Applications

Synthesis of Pharmaceuticals and Natural Products

• Scientific Field : Medicinal Chemistry
• Application Summary : 4-Fluoro-7-azaindole is used in the synthesis of azaindoles and azaindolines, which are important core structures in pharmaceuticals and natural products.
• Methods of Application : A novel one-pot method was developed for selectively synthesizing 7-azaindoles and 7-azaindolines. The reactions occur between the readily available 2-fluoro-3-methylpyridine and arylaldehydes.
• Results : The chemoselectivity is counterion dependent, with LiN (SiMe3)2 generating 7-azaindolines and KN (SiMe3)2 furnishing 7-azaindoles.

Drug Discovery

• Scientific Field : Drug Discovery
• Application Summary : The 7-azaindole building block, which can be synthesized from 4-Fluoro-7-azaindole, has attracted considerable interest in the field of drug discovery.
• Methods of Application : Advances in metal-catalyzed chemistry have supported the development of a number of novel and effective methods for functionalization of the 7-azaindole template.
• Results : This has led to the development of synthetic, elegant techniques for the functionalization of 7-azaindoles.

Development of Organic Semiconductors

• Scientific Field : Material Science
• Application Summary : 4-Fluoro-7-azaindole has been used as a building block in the synthesis of organic semiconductors.
• Methods of Application : The specific methods of application or experimental procedures were not detailed in the source.
• Results : These organic semiconductors are important components in the development of electronic devices such as solar cells and transistors.

DNA Study and Understanding Mutagenic Behavior

• Scientific Field : Biochemistry
• Application Summary : The 7-azaindole dimer, which can be synthesized from 4-Fluoro-7-azaindole, is a model molecule for DNA study and understanding the mutagenic behavior.
• Methods of Application : The specific methods of application or experimental procedures were not detailed in the source.
• Results : The neutral and protonated forms of 7-azaindole monomer with significant fluorescence intensity fit the fluorescent sensor strategy to recognize selective metal ions.

Synthesis of Bioactive Natural Products and Drug Candidates

• Scientific Field : Organic Chemistry
• Application Summary : The azaindole chemical scaffold, which can be synthesized from 4-Fluoro-7-azaindole, is represented in many biologically active natural products and synthetic derivatives. This chemical scaffold has yielded several therapeutic agents for a variety of diseases.
• Methods of Application : Novel synthetic strategies have been developed for azaindole core units. Using these strategies, a number of diversely substituted azaindoles including bioactive natural products, key intermediates, and drug candidates have been produced.
• Results : The novel synthetic strategies developed for azaindoles have highlighted their attractive reaction mechanisms, advantages, and limitations.

Synthesis of Tyrosine Kinase Inhibitors

• Scientific Field : Medicinal Chemistry
• Application Summary : 4-Bromo-7-azaindole, which can be synthesized from 4-Fluoro-7-azaindole, is used as a chemical reagent in the synthesis of tyrosine kinase inhibitors. Tyrosine kinase inhibitors are a class of drugs that target specific enzymes involved in cell growth and division, and are commonly used in the treatment of cancer.
• Methods of Application : The specific methods of application or experimental procedures were not detailed in the source.
• Results : The use of 4-Bromo-7-azaindole in the synthesis of tyrosine kinase inhibitors has contributed to the development of effective treatments for cancer.

Synthesis of Azaindoles from Pyridine and Pyrrole Building Blocks

• Scientific Field : Organic Chemistry
• Application Summary : The azaindole chemical scaffold, which can be synthesized from 4-Fluoro-7-azaindole, is represented in many biologically active natural products and synthetic derivatives. This chemical scaffold has yielded several therapeutic agents for a variety of diseases.
• Methods of Application : Novel synthetic strategies have been developed for azaindole core units. Using these strategies, a number of diversely substituted azaindoles including bioactive natural products, key intermediates, and drug candidates have been produced.
• Results : The novel synthetic strategies developed for azaindoles have highlighted their attractive reaction mechanisms, advantages, and limitations.

Global Ring Functionalization of 7-Azaindoles

• Scientific Field : Medicinal Chemistry
• Application Summary : The 7-azaindole building block, which can be synthesized from 4-Fluoro-7-azaindole, has attracted considerable interest in the field of drug discovery. Because of their powerful medicinal properties, the development of synthetic, elegant techniques for the functionalization of 7-azaindoles continues to be an active area of research.
• Methods of Application : Advances in metal-catalyzed chemistry have recently supported the successful development of a number of novel and effective methods for functionalization of the 7-azaindole template.
• Results : This review reports state-of-the-art functionalization chemistry of 7-azaindoles with an aspiration to highlight the global ring functionalization of 7-azaindoles that are potential as pharmacophores for various therapeutic targets.

Safety And Hazards

4-Fluoro-7-azaindole is considered hazardous. It is advised to avoid dust formation, breathing mist, gas, or vapors, and contacting with skin and eye. Use of personal protective equipment, wearing chemical impermeable gloves, ensuring adequate ventilation, removing all sources of ignition, and evacuating personnel to safe areas are recommended.

Future Directions

The azaindole chemical scaffold, including 4-Fluoro-7-azaindole, has attracted considerable interest in the field of drug discovery. Due to their powerful medicinal properties, the development of synthetic techniques for the functionalization of azaindoles continues to be an active area of research. This may offer potential solutions to develop novel and facile methodologies for the azaindole derivatives of biological interest.

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