36751-46-9

Basic information

• Product Name: 2-(3-bromophenyl)pyrazolo[1,5-a]pyridine
• Synonyms: 2-(3-bromophenyl)pyrazolo[1,5-a]pyridine
• CAS NO: 36751-46-9
• Molecular Weight: 273.132
• Mol File: 36751-46-9.mol

Chemical Properties

• CAS DataBase Reference: 2-(3-bromophenyl)pyrazolo[1,5-a]pyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(3-bromophenyl)pyrazolo[1,5-a]pyridine(36751-46-9)
• EPA Substance Registry System: 2-(3-bromophenyl)pyrazolo[1,5-a]pyridine(36751-46-9)

Safety Data

• Hazardous Substances Data: 36751-46-9(Hazardous Substances Data)

Upstream product

• 25275-41-6 N-iminopyridinium ylide 
• 23031-08-5 benzoyl(pyridin-1-ium-1-yl)amide 
• 174967-37-4 (E)-1-bromo-3-(2-iodovinyl)benzene 
• 110-86-1 pyridine 

Relevant articles and documents

Synthesis of 2- and 2,3-substituted Pyrazolo[1,5- a ]pyridines: Scope and mechanistic considerations of a domino direct alkynylation and cyclization of n -iminopyridinium ylides using alkenyl bromides, alkenyl iodides, and alkynes

Direct functionalization and tandem processes have both received considerable recent interest due to their cost and time efficiency. Herein we report the synthesis of difficult to obtain 2-substituted pyrazolo[1,5-a] pyridines through a tandem palladium-catalyzed/silver-mediated elimination/direct functionalization/cyclization reaction involving N-benzoyliminopyridinium ylides. As such, these biologically important molecules are prepared in an efficient, high-yielding manner, only requiring a two-step sequence from pyridine. Aryl-substituted alkenyl bromides and iodides are effective ylide coupling partners. Mechanistic studies led to the use of terminal alkynes, which extended the scope of the reaction to include alkyl substitution on the unsaturated reactive site. The optimization, scope, and mechanistic considerations of the process are discussed.