Efficient and improved synthesis of Telmisartan

An efficient synthesis of the angiotensin II receptor antagonist Telmisartan (1) is presented involving a cross coupling of 4-formylphenylboronic acid 10 with 2-(2-bromophenyl)-4,4-dimethyl-2-oxazoline (11) as the key step (90% yield). The benzimidazole moiety 15 was constructed regioselectively via...

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Detalles Bibliográficos
Autores principales: Kumar, A Sanjeev, Ghosh, Samir, Mehta, G N
Formato: Texto
Lenguaje:English
Publicado: Beilstein-Institut 2010
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2874342/
https://www.ncbi.nlm.nih.gov/pubmed/20502601
http://dx.doi.org/10.3762/bjoc.6.25
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author Kumar, A Sanjeev
Ghosh, Samir
Mehta, G N
author_facet Kumar, A Sanjeev
Ghosh, Samir
Mehta, G N
author_sort Kumar, A Sanjeev
collection PubMed
description An efficient synthesis of the angiotensin II receptor antagonist Telmisartan (1) is presented involving a cross coupling of 4-formylphenylboronic acid 10 with 2-(2-bromophenyl)-4,4-dimethyl-2-oxazoline (11) as the key step (90% yield). The benzimidazole moiety 15 was constructed regioselectively via a reductive amination-condensation sequence, replacing the alkylation of the preformed benzimidazole step in the previously published route. This methodology overcomes many of drawbacks associated with previously reported syntheses.
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spelling pubmed-28743422010-05-25 Efficient and improved synthesis of Telmisartan Kumar, A Sanjeev Ghosh, Samir Mehta, G N Beilstein J Org Chem Full Research Paper An efficient synthesis of the angiotensin II receptor antagonist Telmisartan (1) is presented involving a cross coupling of 4-formylphenylboronic acid 10 with 2-(2-bromophenyl)-4,4-dimethyl-2-oxazoline (11) as the key step (90% yield). The benzimidazole moiety 15 was constructed regioselectively via a reductive amination-condensation sequence, replacing the alkylation of the preformed benzimidazole step in the previously published route. This methodology overcomes many of drawbacks associated with previously reported syntheses. Beilstein-Institut 2010-03-11 /pmc/articles/PMC2874342/ /pubmed/20502601 http://dx.doi.org/10.3762/bjoc.6.25 Text en Copyright © 2010, Kumar et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Kumar, A Sanjeev
Ghosh, Samir
Mehta, G N
Efficient and improved synthesis of Telmisartan
title Efficient and improved synthesis of Telmisartan
title_full Efficient and improved synthesis of Telmisartan
title_fullStr Efficient and improved synthesis of Telmisartan
title_full_unstemmed Efficient and improved synthesis of Telmisartan
title_short Efficient and improved synthesis of Telmisartan
title_sort efficient and improved synthesis of telmisartan
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2874342/
https://www.ncbi.nlm.nih.gov/pubmed/20502601
http://dx.doi.org/10.3762/bjoc.6.25
work_keys_str_mv AT kumarasanjeev efficientandimprovedsynthesisoftelmisartan
AT ghoshsamir efficientandimprovedsynthesisoftelmisartan
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