10592-27-5

Usage

Uses

Used in Pharmaceutical Industry:
2,3-DIHYDRO-1H-PYRROLO[2,3-B]PYRIDINE is used as a pharmaceutical raw material and intermediate for the development of various drugs. Its unique chemical structure allows it to be a potential candidate for the synthesis of new pharmaceutical compounds with therapeutic applications.
Used in Chemical Research:
2,3-DIHYDRO-1H-PYRROLO[2,3-B]PYRIDINE can also be used in chemical research for studying its properties and potential applications in various fields. Its chemical structure can provide insights into the development of new compounds and materials with specific functions and characteristics.

InChI:InChI=1/C7H8N2/c1-2-6-3-5-9-7(6)8-4-1/h1-2,4H,3,5H2,(H,8,9)

Upstream product

• 271-63-6 7-Azaindole 
• 110167-08-3 3-(3-butynyl-1-amino)-1,2,4-triazine 
• 111097-51-9 2-(N-acetyl-3-butynylamino)pyrimidine 
• 52200-48-3 3-bromo-2-chloropyridine 
• 54230-88-5 8-bromotetrazolo[1,5-a]pyridine 
• 138343-75-6 tert-butyl (3-methylpyridin-2-yl)carbamate 
• 1603-40-3 3-methylpyridin-2-ylamine 
• 111097-54-2 N-(but-3-yn-1-yl)pyrimidin-2-amine 

Downstream Products

• 115170-40-6 7-aza-5-bromoindoline 
• 118600-53-6 5-nitro-7-azaindoline 
• 1616337-39-3 C₂₆H₂₄N₂ 
• 1609172-17-9 1-(4-bromophenylsulfonyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine 
• 1609171-98-3 (E)-3-(4-(2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-ylsulfonyl)phenyl)-N-hydroxyacrylamide 
• 1609171-97-2 (E)-3-(3-(2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-ylsulfonyl)phenyl)-N-hydroxyacrylamide 

Relevant academic research and scientific papers

Iron-Catalyzed Amination of Strong Aliphatic C(sp3)-H Bonds

A concept for intramolecular denitrogenative C(sp3)-H amination of 1,2,3,4-tetrazoles bearing unactivated primary, secondary, and tertiary C-H bonds is discovered. This catalytic amination follows an unprecedented metalloradical activation mechanism. The utility of the method is showcased with the short synthesis of a bioactive molecule. Moreover, an initial effort has been embarked on for the enantioselective C(sp3)-H amination through the catalyst design. Collectively, this study underlines the development of C(sp3)-H bond functionalization chemistry that should find wide application in the context of drug discovery and natural product synthesis.

Synthesis method of 5-bromo-7-azaindole

The invention relates to a synthesis method of 5-bromo-7-azaindole. With 7-azaindole as a raw material, conjugation of the five-membered ring of indole is damaged by low-pressure liquid-phase hydrogenation, and a key medical intermediate 5-bromo-7-azaindole is prepared through oxybromination and nonmetal oxydehydrogenation. The product purity is higher than or equal to 99%. Bromine atoms are introduced by an oxybromination technology, the utilization rate of the bromine atoms exceeds 98%, the use of bromine is avoided, and the problem that a large amount of bromine-containing waste liquid is generated in original technology is solved. According to the synthesis method provided by the invention, through nonmetal catalytic dehydrogenation, heavy metal catalysis is avoided, the problem of heavy metal residue easily occurring in the product is solved, and the safety of medicine products is ensured. The reaction efficiency can be effectively improved, the reaction time is shortened, and thetotal reaction yield is increased; moreover, industrial waste liquid and residue is reduced, industrial popularization is facilitated, and remarkably high economic benefits are created.

Sustainable Radical Cascades to Synthesize Difluoroalkylated Pyrrolo[1,2-a]indoles

We disclose herein a photocatalytic difluoroalkylation and cyclization cascade reaction of N-(but-2-enoyl)indoles with broad substrate scopes in up to 90% isolated yield. This method provides sustainable and efficient access to synthesize difluoroalkylated pyrrolo[1,2-a]indoles with a quaternary carbon center under mild conditions.

Palladium-metalated porous organic polymers as recyclable catalysts for chemoselective decarbonylation of aldehydes

A novel palladium nanoparticle (NP)-metalated porous organic ligand (Pd NPs/POL-xantphos) has been prepared for the chemoselective decarbonylation of aldehydes. This heterogenous catalyst not only has excellent catalytic activity and chemoselectivity, but also holds high activity after 10 runs of reuse. The effective usage of this method is demonstrated through the synthesis of biofuels such as furfuryl alcohol (FFA) via the highly chemoselective decarbonylation of biomass-derived 5-hydroxy-methylfurfural (HMF) with a TON up to 1540. More importantly, 9-fluorenone could be obtained in one step through the decarbonylation of 2-bromobenzaldehyde by using this heterogeneous catalyst.

Synthesis method of 5-chloro-7-azaindole

The invention provides a synthesis method of 5-chloro-7-azaindole. The synthesis method comprises the following steps: (1) reacting a dilithium initiator and trimethylbromosilane to prepare silicon-containing organic lithium; (2) reacting 2-amino-3-methylpyridine and di-tert-butyl dicarbonate to prepare 2-N-BOC-amino-3-methylpyridine; (3) performing lithiation on the 2-N-BOC-amino-3-methylpyridine through the silicon-containing organic lithium, and performing delithiation activation, cyclization and dehydration to prepare 7-azaindole; (4) performing hydrogenation reduction reaction on the 7-azaindole to generate 2,3-dihydro-7-azaindole; (5) performing chlorination reaction on the 2,3-dihydro-7-azaindole through liquid chlorine to generate 5-chloro-2,3-dihydro-7-azaindole; and (6) performing dehydrogenation reaction on the 5-chloro-2,3-dihydro-7-azaindole to obtain 5-chloro-7-azaindole. The synthesis method provided by the invention has the advantages of mild conditions and high yield.

α-Halo Amides as Competent Latent Enolates: Direct Catalytic Asymmetric Mannich-Type Reaction

α-Halogenated carbonyl compounds are susceptible to dehalogenation and thus largely neglected as enolate precursors in catalytic enantioselective C-C bond-forming reactions. By merging the increased stability of the α-C-halogen bond of amides and the direct enolization methodology of the designed amide, we explored a direct catalytic asymmetric Mannich-type reaction of α-halo 7-azaindoline amides with N-carbamoyl imines. All α-halo substituents, α-F, -Cl, -Br, -I amides, were tolerated to provide the Mannich-adducts in a highly stereoselective manner without undesirable dehalogenation. The diastereoselectivity switched intriguingly depending on the substitution pattern of the aromatic imines, which is ascribed to stereochemical differentiation based on the open transition-state model. Functional group interconversion of the 7-azaindoline amide moiety of the Mannich-adducts and further elaboration into a diamide without dehalogenation highlight the synthetic utility of the present protocol for accessing enantioenriched halogenated chemical entities.

Production process of 5-bromo-7-azaindole

The invention relates to a production process of 5-bromo-7-azaindole. The production process includes following steps: (1), using 7-azaindole as a raw material, and enabling 7-azaindole to be in catalytic hydrogenation under action of a catalyst-palladium loaded mesoporous carbon to generate dihydro-7-azaindole; (2), enabling dihydro-7-azaindole to be in bromination reaction under action of hydrogen bromide and hydrogen peroxide to generate dihydro-5-bromo-7-azaindole, where a feeding molar ratio of dihydro-7-azaindole, hydrogen bromide and hydrogen peroxide is 1:10-30:1-2, and temperature for bromination reaction is 20-30 DEG C; (3), enabling dihydro-5-bromo-7-azaindole to be in oxidative dehydrogenation under action of manganese dioxide/glacial acetic acid to generate 5-bromo-7-azaindole. The production process has the advantages of high reaction yield and low cost.

Synthesis method of 5-bromo-7-azaindole

The invention discloses a synthesis method of 5-bromo-7-azaindole. With 7-azaindole as the raw material, hydrogenation reduction, bromination and dehydrogenation are conducted, a platinum-carbon catalyst is added for catalyzing 7-azaindole to conduct hydrogenation to prepare dihydro-7-azaindole, catalysis efficiency is improved, and reaction energy consumption and reaction time are decreased; 5-bromo-7-azaindoline is synthesized by adding sodium bromide for catalysis, a mixture of chromic oxide, zinc oxide and magnesium oxide is added for substituting manganese dioxide for catalytic dehydrogenation reaction, reaction time can be effectively shortened, and reaction yield is increased. By means of the method, reaction efficiency can be effectively improved, reaction time is shortened, the total reaction yield is increased, process waste liquid and waste slag are reduced, industrial popularization is facilitated, and extremely high economic benefits are achieved.

A 5-bromo-7-aza-indole synthesis process (by machine translation)

This invention relates to a kind of 5-bromo-7-aza-indole synthesis process, the steps of: the 7-aza indole, Raney nickel, ethanol stirring and hydrogen; reacting filtering, the filter cake is washed with ethanol washing, combined filtrate, concentrated dry, be 7-aza indole [...] ; the crude product with toluene-P-sulfonic acid, methylene chloride mixed, and stirring instillment bromide ; sodium hyposulfite washing the reaction solution, the organic phase is dried with anhydrous sodium sulfate, concentrated to obtain 5-bromo-7-aza-indoline product; the product is dissolved in toluene, adding manganese dioxide, heating reflux reaction; filtering the reaction liquid, the filter cake washed with methylene chloride, combined organic phase, dried, concentrated to obtain 5-bromo-7-azaindoles crude, PE/EA mixed solution for crystallization to obtain the finished product. The invention has the advantages of low cost, simple process, the operation is simple, and the like, is suitable for large-scale factory production, this method generating the purity of the product in 99% or more, the yield of 74% or more, comprehensive utilization rate is high. (by machine translation)

AZAINDOLE GLUCOKINASE ACTIVATORS

Provided herein are compounds of the formula (I): as well as pharmaceutically acceptable salts thereof, wherein the substituents are as those disclosed in the specification. These compounds, and the pharmaceutical compositions containing them, are useful for the treatment of metabolic diseases and disorders such as, for example, type II diabetes mellitus.