1015609-91-2

Basic information

• Product Name: 4-((TRIMETHYLSILYL)ETHYNYL)-1H-PYRROLO[2,3-B]PYRIDINE
• Synonyms: 4-((TRIMETHYLSILYL)ETHYNYL)-1H-PYRROLO[2,3-B]PYRIDINE
• CAS NO: 1015609-91-2
• Molecular Formula: C₁₂H₁₄N₂Si
• Molecular Weight: 214.33846
• Mol File: 1015609-91-2.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4-((TRIMETHYLSILYL)ETHYNYL)-1H-PYRROLO[2,3-B]PYRIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-((TRIMETHYLSILYL)ETHYNYL)-1H-PYRROLO[2,3-B]PYRIDINE(1015609-91-2)
• EPA Substance Registry System: 4-((TRIMETHYLSILYL)ETHYNYL)-1H-PYRROLO[2,3-B]PYRIDINE(1015609-91-2)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 22
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 1015609-91-2(Hazardous Substances Data)

Usage

General Description

4-((Trimethylsilyl)ethynyl)-1H-pyrrolo[2,3-b]pyridine is a chemical compound with the molecular formula C14H15N3Si. It is a pyrrolopyridine derivative with a trimethylsilylethynyl group attached to the pyrrolopyridine ring. 4-((TRIMETHYLSILYL)ETHYNYL)-1H-PYRROLO[2,3-B]PYRIDINE is used in organic synthesis and materials science as a building block for the preparation of various functionalized derivatives. It is also used as a precursor for the synthesis of pharmaceutical compounds and in the development of new materials for electronics and optoelectronics applications. Additionally, it has potential applications in the field of medicinal chemistry as a scaffold for the design of novel drug candidates.

Upstream product

• 319474-34-5 4-iodo-1H-pyrrolo[2,3-b]pyridine 
• 1066-54-2 trimethylsilylacetylene 
• 348640-06-2 4-bromo-7-azaindole 
• 55052-24-9 1H-Pyrrolo[2,3-b]pyridine-7-oxide 
• 271-63-6 7-Azaindole 

Downstream Products

• 1174296-52-6 N-tert-Butyl-2-[2-(1H-pyrrolo[2,3-b]pyridin-4-ylethynyl)-phenyl]-acetamide 
• 1174296-51-5 [2-(1H-pyrrolo[2,3-b]pyridin-4-ylethynyl)-phenyl]-acetic acid 
• 1174296-23-1 4-fluoro-2-(1H-pyrrolo[2,3-b]pyridin-4-ylethynyl)benzonitrile 
• 1243324-22-2 N-{3-[(4-ethynyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-hydroxy-methyl]-2,4-difluoro-phenyl}-4-trifluoromethyl-benzenesulfonamide 

Relevant articles and documents

A one-pot three-component synthesis of fused Spiro-Indoline/Indene derivatives derived from ethynyl azaindole by 1,3-dipolar cycloaddition reaction

A one-pot method for the simple, efficient, and environmentally benign protocol for the synthesis of Spiro-Indoline/Indene derivatives containing Aza indole moiety as a side chain is outlined. The 1,3-dipolar cycloaddition reaction of azomethine ylides derived from ethynyl Azaindole under mild conditions is accomplished. The low cost, easy availability of the starting material, and simple reaction conditions suggest the possible use of the present method for large-scale preparations.

Synthesis of novel 7-azaindole derivatives containing pyridin-3-ylmethyl dithiocarbamate moiety as potent PKM2 activators and PKM2 nucleus translocation inhibitors

Multiple lines of evidence have indicated that pyruvate kinase M2 (PKM2) is upregulated in most cancer cells and it is increasingly recognized as a potential therapeutic target in oncology. In a continuation of our discovery of lead compound 5 and SAR study, the 7-azaindole moiety in compound 5 was systematically optimized. The results showed that compound 6f, which has a difluoroethyl substitution on the 7-azaindole ring, exhibited high PKM2 activation potency and anti-proliferation activities on A375 cell lines. In a xenograft mouse model, oral administration of compound 6f led to significant tumor regression without obvious toxicity. Further mechanistic studies revealed that 6f could influence the translocation of PKM2 into nucleus, as well as induction of apoptosis and autophagy of A375 cells. More importantly, compound 6f significantly inhibited migration of A375 cells in a concentration-dependent manner. Collectively, 6f may serve as a lead compound in the development of potent PKM2 activators for cancer therapy.

Multistep synthesis of a new tricyclic azaindole-based scaffold

In this Letter the synthetic pathway adopted for the preparation of a new functionalized tricyclic scaffold containing the 7-azaindole moiety is presented. An intramolecular palladium-mediated reaction is described as the crucial step for a condensed seve