910791-85-4

Upstream product

• 98-80-6 phenylboronic acid 
• 157020-26-3 pyridinium N-<2'-(5'-bromopyridyl)>aminide 
• 948888-34-4 N-(5-phenylpyridin-2-yl)pyridin-1-ium-1-aminide 
• 148292-03-9 pyridinium N-<2'-(3',5'-dibromopyridyl)>aminide 

Downstream Products

• 33421-40-8 5-phenyl-pyridin-2-ylamine 
• 1087036-90-5 N-[(3'-bromo-5'-phenylpyridin-2'-yl)-(4''-methylbenzoyl)-amino]pyridinium chloride 
• 1224592-63-5 N-[5-phenyl-3-(thiophen-3-yl)pyridin-2-yl]pyridinium aminide 
• 1224592-65-7 N-[3-(benzo[b]thiophen-3-yl)-5-phenylpyridin-2-yl]pyridinium aminide 
• 107351-80-4 2-amino-3-bromo-5-phenylpyridine 
• 1357588-92-1 3-bromo-5-(phenyl)-2(1H)-pyridinone 

Relevant academic research and scientific papers

A facile synthesis of 3,5-halo and aryl 1H-pyridin-2-ones from pyridinium N-(pyridin-2-yl)aminide

The synthesis of halogenated and arylated 1H-pyridin-2-ones starting from pyridinium N-(pyridin-2-yl)aminides is described. The synthetic pathway involves the reaction of pyridinium N-(5-bromopyridin-2-yl)aminide, N-(3-bromo-5- chloropyridin-2-yl)aminide or N-(3,5-dibromopyridin-2-yl)aminide with different boronic acids to afford monosubstituted and disubstituted aminides in good yields. An additional bromination in the 3-position of N-(5-arylpyridin-2-yl) aminides was performed. Finally, reduction of the N-N bond followed by the reaction of the corresponding 2-aminopyridines with sodium nitrite/sulfuric acid in water yields 3,5-disubstituted 1H-pyridin-2-ones in good yields.

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.

A new class of pyrazolopyridine nucleus with fluorescent properties, obtained through either a radical or a Pd arylation pathway from N-azinylpyridinium N-aminides

(Chemical Equation Presented) The synthesis of dipyridopyrazole and pyridopyrazolopyrazine derivatives - both of which incorporate a 3-aryl moiety - can be achieved in moderate yields by intramolecular radical arylation of pyridinium N-aminides using tris(trimethylsilyl)silane and azobisisobutyronitrile. Improved results were obtained on using Pd direct arylation in conjunction with microwave irradiation. A preliminary study into the fluorescent properties of the target compounds is also reported.

Regioselective Suzuki coupling on pyridinium N-(3,5-dibromoheteroar-2-yl)aminides

A regioselective Suzuki-Miyaura cross-coupling reaction on 3′,5′-dibromo pyridinium N-(2′-azinyl)aminides is reported. A series of 3′-aryl(or heteroaryl)-5′-bromo-pyridinium N-(2′-pirazinyl)aminides were obtained in good yields. Two isomeric 3′,5′-diaryl