A Practical Synthesis of 4-Amino-2-(Trifluoromethyl)nicotinic Acid

Autor:	John F. Sagal, Lacey Samp, Daniel P. Walker, Ming Kang, F. Christopher Bi, Richard A. Buzon, Zhijun Zhang, Bryan Li, Robert M. Oliver
Rok vydání:	2010
Předmět:	Carbamate Trifluoromethyl medicine.medical_treatment Organic Chemistry Halogenation chemistry.chemical_element chemistry.chemical_compound chemistry Carboxylation Yield (chemistry) Pyridine medicine Organic chemistry Lithium Amination
Zdroj:	Synlett. 2010:2133-2135
ISSN:	1437-2096 0936-5214
Popis:	A practical synthesis of 4-amino-2-(trifluoromethyl)-nicotinic acid is described. 2-(Trifluoromethyl)pyridine was lithiated using lithium 2,2,6,6-tetramethylpiperidide (LTMP) in the presence of 1,3-dimethyl-2-imidazolidinone (DMI) and followed by CO 2 quench to give the C-3 carboxylation product. Subsequent directed C-4 lithiation of carboxylation product afforded 4-iodo-2-(trifluoromethyl)nicotinic acid, which was coupled with tert-butyl carbamate under Pd-catalyzed conditions and followed by Boc deprotection to yield the title product in four steps and 50% overall yield.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::c392c1b3475470a8aea9646bd02480e7 https://doi.org/10.1055/s-0030-1258481 Zobrazit plný text záznamu