Highly Selective Synthesis of 2-(2H-1,2,3-Triazol-2-yl)benzoic Acids
1
Chemistry Process R&D, Idorsia Pharmaceuticals Ltd., Hegenheimermattweg 91, CH−4123 Allschwil, Switzerland
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Publication type: Journal Article
Publication date: 2019-01-18
scimago Q1
wos Q1
SJR: 0.865
CiteScore: 5.4
Impact factor: 3.5
ISSN: 10836160, 1520586X
Organic Chemistry
Physical and Theoretical Chemistry
Abstract
A selective and scalable synthesis of 2-(2H-1,2,3-triazol-2-yl)benzoic acid starting from 1-fluoro-2-nitrobenzene derivatives is presented. The four-step synthesis introduces the triazole at the start via N2-arylation of 4,5-dibromo-2H-1,2,3-triazole. A sequence of consecutive functional group transformations, namely hydrogenation, Sandmeyer iodination, and Grignard carboxylation, provides the target molecules in a reliable and scalable manner. The usefulness of this method is demonstrated by the synthesis of di- or tri(2H-1,2,3-triazol-2-yl)benzene derivatives, which are difficult to produce by other methods.
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Roth R. et al. Highly Selective Synthesis of 2-(2H-1,2,3-Triazol-2-yl)benzoic Acids // Organic Process Research and Development. 2019. Vol. 23. No. 2. pp. 234-243.
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Roth R., Schmidt G., Prudhomme A., Abele S. Highly Selective Synthesis of 2-(2H-1,2,3-Triazol-2-yl)benzoic Acids // Organic Process Research and Development. 2019. Vol. 23. No. 2. pp. 234-243.
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TY - JOUR
DO - 10.1021/acs.oprd.8b00349
UR - https://doi.org/10.1021/acs.oprd.8b00349
TI - Highly Selective Synthesis of 2-(2H-1,2,3-Triazol-2-yl)benzoic Acids
T2 - Organic Process Research and Development
AU - Roth, Remo
AU - Schmidt, Gunther
AU - Prudhomme, Alice
AU - Abele, Stefan
PY - 2019
DA - 2019/01/18
PB - American Chemical Society (ACS)
SP - 234-243
IS - 2
VL - 23
SN - 1083-6160
SN - 1520-586X
ER -
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BibTex (up to 50 authors)
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@article{2019_Roth,
author = {Remo Roth and Gunther Schmidt and Alice Prudhomme and Stefan Abele},
title = {Highly Selective Synthesis of 2-(2H-1,2,3-Triazol-2-yl)benzoic Acids},
journal = {Organic Process Research and Development},
year = {2019},
volume = {23},
publisher = {American Chemical Society (ACS)},
month = {jan},
url = {https://doi.org/10.1021/acs.oprd.8b00349},
number = {2},
pages = {234--243},
doi = {10.1021/acs.oprd.8b00349}
}
Cite this
MLA
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Roth, Remo, et al. “Highly Selective Synthesis of 2-(2H-1,2,3-Triazol-2-yl)benzoic Acids.” Organic Process Research and Development, vol. 23, no. 2, Jan. 2019, pp. 234-243. https://doi.org/10.1021/acs.oprd.8b00349.