2022 journal article
Synthesis of MAPA Reagents and 2-Alkyl(aryl)aminopyridines from 2-Bromopyridine Using the Goldberg Reaction
MOLECULES, 27(6).
author 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
MeSH headings : Amides; Aminopyridines; Catalysis; Hydrolysis; Indicators and Reagents
www.mdpi.com (publisher PDF)
UN Sustainable Development Goal Categories
3. Good Health and Well-being
(Web of Science)
Source: Web Of Science
Added: April 11, 2022
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.