63237-84-3

Usage

Uses

Used in Organic Synthesis:
Methyl Pyrazolo[1,5-a]pyridine-3-carboxylate is used as a key intermediate in the synthesis of complex organic molecules, contributing to the formation of various chemical structures.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, Methyl Pyrazolo[1,5-a]pyridine-3-carboxylate is used as a core structure for the design and development of new drugs, potentially leading to the creation of novel therapeutic agents.
Used in Pharmaceutical Research:
Methyl Pyrazolo[1,5-a]pyridine-3-carboxylate is employed in pharmaceutical research as a component in the synthesis of potential drug candidates, aiding in the advancement of new treatment options for various medical conditions.

InChI:InChI=1/C9H8N2O2/c1-13-9(12)7-6-10-11-5-3-2-4-8(7)11/h2-6H,1H3

Upstream product

• 39996-41-3 1-aminopyridinium mesitylenesulphonate 
• 922-67-8 propynoic acid methyl ester 
• 623-47-2 propynoic acid ethyl ester 
• 681858-78-6 methyl 3-(dimethylamino)-2-(pyridin-2-yl)acrylate 
• 1658-42-0 methyl 2-pyridylacetate 
• 6295-87-0 N-aminopyridin-1-ium iodide 

Downstream Products

• 274-56-6 3-azaindolizine 

Relevant academic research and scientific papers

Novel bipyrazolo[1,5-: A] pyridine luminogens with aggregation-induced emission enhancement properties

A novel 3,3′-bipyrazolo[1,5-a]pyridine molecular scaffold was obtained as a product of serendipity. Both photophysical characterisations and HOMO-LUMO theoretical calculations indicate its potential as a promising fluorophore with notable intramolecular charge transfer. Nonetheless, the emission properties of this compound suffer from the typical aggregation-caused quenching effect. To overcome this situation, we introduced additional diaryl groups onto the skeleton and synthesised a series of 7,7′-diaryl-3,3′-bipyrazolo[1,5-a]pyridines via palladium-catalysed intermolecular C-H/C-H bond cross-coupling reaction in 35-62% yields. This series of tailor-made luminogens with twisted π-structures display aggregation-induced emission enhancement properties.

Divergent and Regioselective Synthesis of Pyrazolo[1,5- a]pyridines and Imidazo[1,5- a]pyridines

Nitrogenous heterocycles are ubiquitous in pharmaceuticals and drug-like compounds; however, regioselective synthesis has proved challenging. Herein we report our efforts to develop a regioselective method for the synthesis of pyrazolo[1,5-a]pyridines and the serendipitous discovery of a protocol for the regioselective formation of imidazo[1,5-a]pyridines. Together, these transformations allow for the rapid and selective formation of two important heterocyclic motifs from a common intermediate.

Unexpected cleavage of the Cpy-Cpybond in the reaction of 2,2′-bipyridine N,N′-diimines with acetylenes

An unusual cleavage of the Cpy-Cpybond in the reaction of 2,2′-bipyridine N,N′-diimine and its C-methyl substituted derivatives with acetylenes is described. The effect of the solvent on the yield of 7,7′-bipyrazolo[1,5-a]pyridine-2,2′,3,3′-tetracarboxylates and the products of cleavage of the Cpy-Cpybond has been studied. The mechanism of the cleavage reaction is discussed on the basis of DFT calculations.

Acid-Catalyzed Reactions of 3-(Hydroxymethyl)- and 3-(1-Hydroxyethyl)pyrazolopyridines

Treatment of 3-(hydroxymethyl)pyrazolopyridines with trifluoroacetic acid in refluxing dichloromethane led to the formation of bis(pyrazolopyrid-3-yl)methanes or bis pyrid-3-yl)>methyl ethers depending upon the concentration of trifluoroacetic acid.In contrast, similar treatment of 3-(1-hydroxyethyl)pyrazolopyridines gave a mixture of 3-vinylpyrazolopyridines and 1,3-bis(pyrazolopyrid-3-yl)-1-butenes.