A Practical Synthesis of 4-Amino-2-(Trifluoromethyl)nicotinic Acid
Publication type: Journal Article
Publication date: 2010-07-09
scimago Q3
wos Q3
SJR: 0.437
CiteScore: 3.3
Impact factor: 1.4
ISSN: 09365214, 14372096
Organic Chemistry
Abstract
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.
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Li B. et al. A Practical Synthesis of 4-Amino-2-(Trifluoromethyl)nicotinic Acid // Synlett. 2010. Vol. 2010. No. 14. pp. 2133-2135.
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Li B., Bi F., Buzon R., Kang M., Oliver R., Sagal J., Samp L., Walker D., Zhang Z. A Practical Synthesis of 4-Amino-2-(Trifluoromethyl)nicotinic Acid // Synlett. 2010. Vol. 2010. No. 14. pp. 2133-2135.
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TY - JOUR
DO - 10.1055/s-0030-1258481
UR - https://doi.org/10.1055/s-0030-1258481
TI - A Practical Synthesis of 4-Amino-2-(Trifluoromethyl)nicotinic Acid
T2 - Synlett
AU - Li, Bryan
AU - Bi, F.
AU - Buzon, Richard
AU - Kang, Ming
AU - Oliver, Robert
AU - Sagal, John
AU - Samp, Lacey
AU - Walker, Daniel
AU - Zhang, Zhijun
PY - 2010
DA - 2010/07/09
PB - Georg Thieme Verlag KG
SP - 2133-2135
IS - 14
VL - 2010
SN - 0936-5214
SN - 1437-2096
ER -
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BibTex (up to 50 authors)
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@article{2010_Li,
author = {Bryan Li and F. Bi and Richard Buzon and Ming Kang and Robert Oliver and John Sagal and Lacey Samp and Daniel Walker and Zhijun Zhang},
title = {A Practical Synthesis of 4-Amino-2-(Trifluoromethyl)nicotinic Acid},
journal = {Synlett},
year = {2010},
volume = {2010},
publisher = {Georg Thieme Verlag KG},
month = {jul},
url = {https://doi.org/10.1055/s-0030-1258481},
number = {14},
pages = {2133--2135},
doi = {10.1055/s-0030-1258481}
}
Cite this
MLA
Copy
Li, Bryan, et al. “A Practical Synthesis of 4-Amino-2-(Trifluoromethyl)nicotinic Acid.” Synlett, vol. 2010, no. 14, Jul. 2010, pp. 2133-2135. https://doi.org/10.1055/s-0030-1258481.