Products Cited in Publications Worldwide Synthesis of MAPA reagents and 2-alkyl (aryl) aminopyridines from 2-bromopyridine using the goldberg reaction

Synthesis of MAPA reagents and 2-alkyl (aryl) aminopyridines from 2-bromopyridine using the goldberg reaction

Comins, Daniel L

DOI: PMID:

Abstract

A short and economical synthesis of various 2-methylaminopyidine amides (MAPA) from 2-bromopyridine has been developed using the catalytic Goldberg reaction. The effective catalyst was formed in situ by the reaction of CuI and 1,10-phenanthroline in a 1/1 ratio with a final loading of 0.5–3 mol%. The process affords high yields and can accommodate multigram-scale reactions. A modification of this method provides a new preparation of 2-N-substituted aminopyridines from various secondary N-alkyl(aryl)formamides and 2-bromopyridine. The intermediate aminopyridine formamide is cleaved in situ through methanolysis or hydrolysis to give 2-alkyl(aryl)aminopyridines in high yields.

Keywords

N-methyl-N-(2-pyridyl)formamide ; 2-methylaminopyridine amides ; 2-alkyl(aryl)aminopyridines ; Goldberg reaction ; copper-catalyzed reactions ; cross-coupling reactions ; 1,10-phenanthroline

Purchased from AmBeed

A664538123-39-799%

N-Methylformamide

110.0/1kg

Detail

A739104109-04-699%

2-Bromopyridine

137.0/1kg

Detail