866545-91-7

Usage

Uses

Used in Organic Synthesis:
1H-Pyrrolo[2,3-b]pyridine, 1-[(4-methylphenyl)sulfonyl]-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)is used as a building block for the creation of complex organic molecules, leveraging its unique structural features to facilitate the synthesis of a wide array of compounds.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 1H-Pyrrolo[2,3-b]pyridine, 1-[(4-methylphenyl)sulfonyl]-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- serves as a valuable intermediate for the development of new drugs, given its potential to be modified and functionalized, contributing to the discovery of novel therapeutic agents.
Used in Suzuki-Miyaura Cross-Coupling Reactions:
As a reagent in Suzuki-Miyaura cross-coupling reactions, 1H-Pyrrolo[2,3-b]pyridine, 1-[(4-methylphenyl)sulfonyl]-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)is instrumental in the formation of carbon-carbon bonds, a critical process in the synthesis of various organic compounds, including those with potential applications in material science and medicinal chemistry.
Used in Chemical Research:
In the realm of chemical research, 1H-Pyrrolo[2,3-b]pyridine, 1-[(4-methylphenyl)sulfonyl]-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- is utilized for studying reaction mechanisms and exploring new methods of synthesis, further expanding the boundaries of organic chemistry and its applications.

InChI:InChI=1/C20H23BN2O4S/c1-14-8-10-15(11-9-14)28(24,25)23-13-17(16-7-6-12-22-18(16)23)21-26-19(2,3)20(4,5)27-21/h6-13H,1-5H3

Upstream product

• 73183-34-3 bis(pinacol)diborane 
• 226085-18-3 3-bromo-1-(4-methylbenzenesulfonyl)-1H-pyrrolo[2,3-b]pyridine 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 882562-39-2 1-(4-methylbenzenesulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-ylboronic acid 
• 271-63-6 7-Azaindole 
• 74420-15-8 3-bromo-1H-pyrrolo[2,3-b]pyridine 
• 348640-02-8 1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridine 
• 98-59-9 p-toluenesulfonyl chloride 
• 7732-18-5 water 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 664982-01-8 3-iodo-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine 
• 23616-57-1 3-iodo-1H-pyrrolo[2,3-b]pyridine 

Downstream Products

• 1052631-05-6 C₂₅H₂₁N₅O₂S 
• 944842-54-0 decernotinib 
• 1417421-80-7 (R)-2-methyl-2-(2-(1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-4-ylamino)butanoic acid 
• 1417421-95-4 methyl 2-methyl-2-((2-(1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-4-yl)amino)butanoate 
• 1417421-89-6 C₂₁⁽¹³⁾C₄H₂₅F₃N₄⁽¹⁵⁾N₂O₃S 
• 341998-55-8 Meriolin 1 
• 866545-94-0 3-(6-chloropyrimidin-4-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine 
• 866545-92-8 3-(2-(methylthio)pyrimidin-4-yl)-1-(tolyl-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine 

Relevant academic research and scientific papers

Sequentially Catalyzed Three-Component Masuda-Suzuki-Sonogashira Synthesis of Fluorescent 2-Alkynyl-4-(7-azaindol-3-yl)pyrimidines: Three Palladium-Catalyzed Processes in a One-Pot Fashion

The Masuda-Suzuki-Sonogashira sequence efficiently unites, in a one-pot fashion, a borylation, an arylation, and an alkynylation in the sense of a sequentially Pd-catalyzed three-component reaction to give fluorescent 2-alkynyl-4-(7-azaindol-3-yl) pyrimid

Nature-Inspired (di)Azine-Bridged Bisindole Alkaloids with Potent Antibacterial in Vitro and in Vivo Efficacy against Methicillin-Resistant Staphylococcus aureus

Natural bisindole alkaloids such as Hyrtinadine A and Alocasin A, which are known to exhibit diverse bioactivities, provide promising chemical scaffolds for drug development. By optimizing the Masuda borylation-Suzuki coupling sequence, a library of various natural product-derived and non-natural (di)azine-bridged bisindoles was created. While unsubstituted bisindoles were devoid of antibacterial activity, 5,5′-chloro derivatives were highly active against methicillin-resistant Staphylococcus aureus (MRSA) and further Gram-positive pathogens at minimal inhibitory concentrations ranging from 0.20 to 0.78 μM. These compounds showed strong bactericidal killing effects but only moderate cytotoxicity against human cell lines. Furthermore, the two front-runner compounds 4j and 4n exhibited potent in vivo efficacy against MRSA in a mouse wound infection model. Although structurally related bisindoles were reported to specifically target pyruvate kinase in MRSA, antibacterial activity of 4j and 4n is independent of pyruvate kinase. Rather, these compounds lead to bacterial membrane permeabilization and cellular efflux of low-molecular-weight molecules.

Design, synthesis, biological evaluation and molecular modeling of novel 1H-pyrrolo[2,3-b]pyridine derivatives as potential anti-tumor agents

A class of 3-substituted 1H-pyrrolo[2,3-b]pyridine derivatives were designed, synthesized and evaluated for their in vitro biological activities against maternal embryonic leucine zipper kinase (MELK). Among these derivatives, the optimized compound 16h e

Novel meriolin derivatives as rapid apoptosis inducers

3-(Hetero)aryl substituted 7-azaindoles possessing multikinase inhibitor activity are readily accessed in a one-pot Masuda borylation-Suzuki coupling sequence. Several promising derivatives were identified as apoptosis inducers and, emphasizing the multik

DERIVATIVES OF QUINOLINE AS INHIBITORS OF DYRK1A AND/OR DYRK1B KINASES

The present invention relates to the compound of formula (I) and salts, stereoisomers, tautomers or N-oxides thereof. The present invention is further concerned with the use of such a compound or salt, stereoisomer, tautomer or N-oxide thereof as medicament and a pharmaceutical composition comprising said compound.

Discovery of VX-509 (Decernotinib): A Potent and Selective Janus Kinase 3 Inhibitor for the Treatment of Autoimmune Diseases

While several therapeutic options exist, the need for more effective, safe, and convenient treatment for a variety of autoimmune diseases persists. Targeting the Janus tyrosine kinases (JAKs), which play essential roles in cell signaling responses and can contribute to aberrant immune function associated with disease, has emerged as a novel and attractive approach for the development of new autoimmune disease therapies. We screened our compound library against JAK3, a key signaling kinase in immune cells, and identified multiple scaffolds showing good inhibitory activity for this kinase. A particular scaffold of interest, the 1H-pyrrolo[2,3-b]pyridine series (7-azaindoles), was selected for further optimization in part on the basis of binding affinity (Ki) as well as on the basis of cellular potency. Optimization of this chemical series led to the identification of VX-509 (decernotinib), a novel, potent, and selective JAK3 inhibitor, which demonstrates good efficacy in vivo in the rat host versus graft model (HvG). On the basis of these findings, it appears that VX-509 offers potential for the treatment of a variety of autoimmune diseases.

COMPOUND, ORGANIC OPTOELECTRIC DEVICE AND DISPLAY DEVICE

The present invention relates to a compound, and an organic optoelectronic element and a display device including the same wherein the compound denoted by chemical formula 1 is provided. In chemical formula 1, X1 to X10, L, n and R11 are as defined in the

METHODS FOR TREATING INFLAMMATORY DISEASES AND PHARMACEUTICAL COMBINATIONS USEFUL THEREFOR

The present invention provides a method of treating psoriasis comprising the administration of a compound of Formula I or a compound of Formula I and a co-therapy, and administrations of pharmaceutical compositions comprising a compound of Formula (I).

PHARMACEUTICAL COMBINATIONS USEFUL FOR TREATING RHEUMATOID ARTHRITIS

The present invention provides a method of treating or lessening the severity of a disease or disorder mediated by an abnormal immune response (e.g., rheumatoid arthritis) comprising the administration of a compound of Formula I and a corticosteroid.

PROCESSES AND INTERMEDIATES FOR PRODUCING AZAINDOLES

The present invention relates to processes and intermediates for the preparation of compounds useful as inhibitors of Janus kinases (JAK).