80235-01-4

Usage

Uses

3-chloro-1H-pyrrolo[2,3-b]pyridine is a useful research chemical.

Chemical Properties

Solid

InChI:InChI=1/C7H5ClN2/c8-6-4-10-7-5(6)2-1-3-9-7/h1-4H,(H,9,10)

Upstream product

• 271-63-6 7-Azaindole 

Relevant academic research and scientific papers

A 3 bit halogen-substituted 7 - aza indole preparation method (by machine translation)

The invention discloses a three-position three-halogen-substituted 7 - aza indole preparation method, comprises the following steps: the 7 - aza indole dissolved in organic solvent, adding halogen source compound and catalyst, react under the catalysis of the catalyst, after the reaction, to obtain purified 3 bit halogen-substituted 7 - azaindole. The method uses a three step reaction method for preparing halogen-substituted 7 - azaindole, using multivariate composite catalyst system, the reaction conversion is high, a high degree of selectivity. And, the preparation method required mild reaction conditions, the safety of the raw materials, the reaction and the cost is low, and has high industrial production prospect. (by machine translation)

Story of an Age-Old Reagent: An Electrophilic Chlorination of Arenes and Heterocycles by 1-Chloro-1,2-benziodoxol-3-one

By the use of 1-chloro-1,2-benziodoxol-3-one, an age-old reagent, the practical and efficient chlorination method is achieved. This hypervalent iodine reagent is amenable not only to the chlorination of nitrogen-containing heterocycles but also to selected classes of arenes, BODIPY dyes, and pharmaceuticals. In addition, the advantages, such as easy preparation and recyclable, air- and moisture-stable, in combination with the success in a gram-scale experiment grant this reagent great potential for industrial application.

Simple and efficient procedures for selective preparation of 3-haloindoles and 2,3-dihaloindoles by using 1,3-dibromo-5,5-dimethylhydantoin and 1,3-dichloro-5,5-dimethylhydantoin

Simple and efficient synthetic procedures for the selective preparation of 3-bromo/3-chloroindoles and 2,3-dibromo/2,3-dichloroindoles by using 1,3-dibromo-5,5-dimethylhydantoin (DBDMH) and 1,3-dichloro-5,5-dimethylhydantoin (DCDMH) were developed. Using 1,4-dioxane as the solvent, a variety of indoles, treated with 0.55 equiv DBDMH/DCDMH, afford the corresponding 3-bromo/3-chloroindoles selectively in 82-99% yield. In 1,2-dichloroethane (DCE), a series of 2,3-dichloro/2,3-dibromoindoles were selectively obtained in 84-95% yield by treating with DBDMH/DCDMH. All the processes do not need extra catalysts, dry solvents, or harsh reaction conditions.

Taming chlorine azide: Access to 1,2-azidochlorides from alkenes

The in situ preparation and trapping of chlorine azide provided a versatile one-pot method for the azidochlorination of alkenes. Gaseous ClN3 generated from sodium azide, hypochlorite, and acetic acid can be explosive if isolation is attempted. Instead, we generated the reagent in biphasic media in the presence of olefinic compounds dissolved in the organic layer or evenly emulsified throughout the solution in the absence of organic solvent. Under these conditions, ClN3 is created slowly and trapped immediately at the aqueous-organic interface. The resulting safe and reliable procedure provided 1,2-azidochloride derivatives of a variety of substrates, with evidence for both polar and radical mechanisms. Minor impurities characterized in the product mixtures indicated the presence of alternative reaction pathways deriving primarily from radical intermediates.

A practical synthesis of 2-((1H-pyrrolo[2,3-b]pyridine-4-yl)methylamino)-5- fluoronicotinic acid

A practical synthesis of a key pharmaceutical intermediate, 2-[(1H-pyrrolo[2,3-b]pyridine-4-yl)methylamino]-5-fluoronicotinic acid (1), is described. To introduce the aminomethyl moiety of 2 via a palladium-catalyzed cyanation/reduction sequence, a regioselective chlorination of 7-azaindole via the N-oxide was developed. A highly selective monodechlorination of 2,6-dichloro-5-fluoronicotinic acid was discovered to afford the nicotinic acid 3. The two building blocks 2 and 3 were then coupled to complete the preparation of 1.

Synthesis and Biological Activity of 1H-Pyrrolo[2,3-b]pyridine Derivatives: Correlation between Inhibitory Activity against the Fungus Causing Rice Blast and Ionization Potential

Synthesis and biological activity of a variety of 3- and 6-substituted 1H-pyrrolo[2,3-6]pyridine (7-azaindole) derivatives are described. Many of the synthesized 7-azaindoles exhibited considerable fungicidal activity toward Pyricularia oryzae, a fungus which causes rice blast, in vivo. When quantum parameters of the tested 7-azaindoles were evaluated by semiempirical molecular orbital calculations, a relationship was observed between the activity and the calculated ionization potentials of the 7-azaindole derivatives.