An Improved Synthesis of the Triethylene Glycol-Substituted 4-(N-Methyl-N-Boc-Amino)Styrylpyridine

[Image: see text] An improved five-step synthesis of triethylene glycol-substituted 4-(N-methyl-N-Boc-amino)styrylpyridine (6) is described. Using cost-effective starting materials, the developed synthesis route was synthetic, efficient, and chromatographic purification-free. The key point of the wo...

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Autores principales: Jia, Jianhua, Wei, Huiqiang, Duan, Yuqing, Ning, Hongxin, Yu, Jiang, Zhu, Yuan, Hou, Wenbin, Li, Yiliang
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2020
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7424578/
https://www.ncbi.nlm.nih.gov/pubmed/32803038
http://dx.doi.org/10.1021/acsomega.0c01244
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author Jia, Jianhua
Wei, Huiqiang
Duan, Yuqing
Ning, Hongxin
Yu, Jiang
Zhu, Yuan
Hou, Wenbin
Li, Yiliang
author_facet Jia, Jianhua
Wei, Huiqiang
Duan, Yuqing
Ning, Hongxin
Yu, Jiang
Zhu, Yuan
Hou, Wenbin
Li, Yiliang
author_sort Jia, Jianhua
collection PubMed
description [Image: see text] An improved five-step synthesis of triethylene glycol-substituted 4-(N-methyl-N-Boc-amino)styrylpyridine (6) is described. Using cost-effective starting materials, the developed synthesis route was synthetic, efficient, and chromatographic purification-free. The key point of the work is the one-pot synthesis of tert-butyl methyl(4-vinylphenyl)carbamate through methylation and elimination in the NaH/THF system. The new synthesis route shows the potential to achieve scaled-up preparation of 6 in the future.
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spelling pubmed-74245782020-08-14 An Improved Synthesis of the Triethylene Glycol-Substituted 4-(N-Methyl-N-Boc-Amino)Styrylpyridine Jia, Jianhua Wei, Huiqiang Duan, Yuqing Ning, Hongxin Yu, Jiang Zhu, Yuan Hou, Wenbin Li, Yiliang ACS Omega [Image: see text] An improved five-step synthesis of triethylene glycol-substituted 4-(N-methyl-N-Boc-amino)styrylpyridine (6) is described. Using cost-effective starting materials, the developed synthesis route was synthetic, efficient, and chromatographic purification-free. The key point of the work is the one-pot synthesis of tert-butyl methyl(4-vinylphenyl)carbamate through methylation and elimination in the NaH/THF system. The new synthesis route shows the potential to achieve scaled-up preparation of 6 in the future. American Chemical Society 2020-07-30 /pmc/articles/PMC7424578/ /pubmed/32803038 http://dx.doi.org/10.1021/acsomega.0c01244 Text en Copyright © 2020 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Jia, Jianhua
Wei, Huiqiang
Duan, Yuqing
Ning, Hongxin
Yu, Jiang
Zhu, Yuan
Hou, Wenbin
Li, Yiliang
An Improved Synthesis of the Triethylene Glycol-Substituted 4-(N-Methyl-N-Boc-Amino)Styrylpyridine
title An Improved Synthesis of the Triethylene Glycol-Substituted 4-(N-Methyl-N-Boc-Amino)Styrylpyridine
title_full An Improved Synthesis of the Triethylene Glycol-Substituted 4-(N-Methyl-N-Boc-Amino)Styrylpyridine
title_fullStr An Improved Synthesis of the Triethylene Glycol-Substituted 4-(N-Methyl-N-Boc-Amino)Styrylpyridine
title_full_unstemmed An Improved Synthesis of the Triethylene Glycol-Substituted 4-(N-Methyl-N-Boc-Amino)Styrylpyridine
title_short An Improved Synthesis of the Triethylene Glycol-Substituted 4-(N-Methyl-N-Boc-Amino)Styrylpyridine
title_sort improved synthesis of the triethylene glycol-substituted 4-(n-methyl-n-boc-amino)styrylpyridine
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7424578/
https://www.ncbi.nlm.nih.gov/pubmed/32803038
http://dx.doi.org/10.1021/acsomega.0c01244
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