Synthesis of MAPA Reagents and 2-Alkyl(aryl)aminopyridines from 2-Bromopyridine Using the Goldberg Reaction

Autor:	Daniel L. Comins
Jazyk:	angličtina
Rok vydání:	2022
Předmět:	N-methyl-N-(2-pyridyl)formamide 2-methylaminopyridine amides 2-alkyl(aryl)aminopyridines Goldberg reaction copper-catalyzed reactions cross-coupling reactions Organic chemistry QD241-441
Zdroj:	Molecules, Vol 27, Iss 6, p 1833 (2022)
Druh dokumentu:	article
ISSN:	27061833 1420-3049
DOI:	10.3390/molecules27061833
Popis:	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.
Databáze:	Directory of Open Access Journals
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