1224592-55-5

Basic information

• Product Name: N-[5-(3,5-dimethylphenyl)pyridin-2-yl]pyridinium aminide
• Synonyms: N-[5-(3,5-dimethylphenyl)pyridin-2-yl]pyridinium aminide
• CAS NO: 1224592-55-5
• Molecular Weight: 275.353
• Mol File: 1224592-55-5.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: N-[5-(3,5-dimethylphenyl)pyridin-2-yl]pyridinium aminide(CAS DataBase Reference)
• NIST Chemistry Reference: N-[5-(3,5-dimethylphenyl)pyridin-2-yl]pyridinium aminide(1224592-55-5)
• EPA Substance Registry System: N-[5-(3,5-dimethylphenyl)pyridin-2-yl]pyridinium aminide(1224592-55-5)

Safety Data

• Hazardous Substances Data: 1224592-55-5(Hazardous Substances Data)

Upstream product

• 157020-26-3 pyridinium N-<2'-(5'-bromopyridyl)>aminide 
• 172975-69-8 3,5-dimethylphenyl boronic acid 

Downstream Products

• 1224592-58-8 N-[3-bromo-5-(3,5-dimethylphenyl)pyridin-2-yl]pyridinium aminide 
• 1224592-61-3 N-[3-bromo-5-(4-bromo-3,5-dimethylphenyl)pyridin-2-yl]pyridinium aminide 

Relevant articles and documents

Pd-catalyzed reactions on pyridinium N-heteroarylaminides. Step-by-step synthesis of 3,5-unsymmetrically disubstituted 2-aminopyridines

Suzuki-Miyaura cross-coupling processes on N-pyridinium bromoazinyl aminides allow access to 3,5-disubstituted N-alkyl-2-aminopyridines. The synthetic pathway involves a regioselective bromination of pyridinium N-(pyridin-2-yl)aminide and a subsequent reaction with boronic acids to afford monosubstituted aminides in good yields. An additional bromination in the 5-position of the pyridine ring followed by a coupling reaction gives pyridinium N-(3,5-diarylpyridin-2-yl)aminides. Finally, a regioselective alkylation on the exo-nitrogen and reduction of the N-N bond yields highly substituted 2-aminopyridines.