One‐Pot Synthesis of (11)C‐Labelled Primary Benzamides via Intermediate [(11)C]Aroyl Dimethylaminopyridinium Salts

Electrophilic (11)C‐labelled aroyl dimethylaminopyridinium salts, obtained by carbonylative cross‐coupling of aryl halides with [(11)C]carbon monoxide, were prepared for the first time and shown to be valuable intermediates in the synthesis of primary [(11)C]benzamides. The methodology furnished a s...

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Detalles Bibliográficos
Autores principales: Ferrat, Mélodie, Dahl, Kenneth, Schou, Magnus
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2021
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8251633/
https://www.ncbi.nlm.nih.gov/pubmed/33885193
http://dx.doi.org/10.1002/chem.202100544
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author Ferrat, Mélodie
Dahl, Kenneth
Schou, Magnus
author_facet Ferrat, Mélodie
Dahl, Kenneth
Schou, Magnus
author_sort Ferrat, Mélodie
collection PubMed
description Electrophilic (11)C‐labelled aroyl dimethylaminopyridinium salts, obtained by carbonylative cross‐coupling of aryl halides with [(11)C]carbon monoxide, were prepared for the first time and shown to be valuable intermediates in the synthesis of primary [(11)C]benzamides. The methodology furnished a set of benzamide model compounds, including the two poly (ADP‐ribose) polymerase (PARP) inhibitors niraparib and veliparib, in moderate to excellent radiochemical yields. In addition to providing a convenient and practical route to primary [(11)C]benzamides, the current method paves the way for future application of [(11)C]aroyl dimethylaminopyridinium halide salts in positron emission tomography (PET) tracer synthesis.
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spelling pubmed-82516332021-07-06 One‐Pot Synthesis of (11)C‐Labelled Primary Benzamides via Intermediate [(11)C]Aroyl Dimethylaminopyridinium Salts Ferrat, Mélodie Dahl, Kenneth Schou, Magnus Chemistry Communications Electrophilic (11)C‐labelled aroyl dimethylaminopyridinium salts, obtained by carbonylative cross‐coupling of aryl halides with [(11)C]carbon monoxide, were prepared for the first time and shown to be valuable intermediates in the synthesis of primary [(11)C]benzamides. The methodology furnished a set of benzamide model compounds, including the two poly (ADP‐ribose) polymerase (PARP) inhibitors niraparib and veliparib, in moderate to excellent radiochemical yields. In addition to providing a convenient and practical route to primary [(11)C]benzamides, the current method paves the way for future application of [(11)C]aroyl dimethylaminopyridinium halide salts in positron emission tomography (PET) tracer synthesis. John Wiley and Sons Inc. 2021-06-01 2021-06-16 /pmc/articles/PMC8251633/ /pubmed/33885193 http://dx.doi.org/10.1002/chem.202100544 Text en © 2021 The Authors. Published by Wiley-VCH GmbH https://creativecommons.org/licenses/by-nc-nd/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc-nd/4.0/ (https://creativecommons.org/licenses/by-nc-nd/4.0/) License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non‐commercial and no modifications or adaptations are made.
spellingShingle Communications
Ferrat, Mélodie
Dahl, Kenneth
Schou, Magnus
One‐Pot Synthesis of (11)C‐Labelled Primary Benzamides via Intermediate [(11)C]Aroyl Dimethylaminopyridinium Salts
title One‐Pot Synthesis of (11)C‐Labelled Primary Benzamides via Intermediate [(11)C]Aroyl Dimethylaminopyridinium Salts
title_full One‐Pot Synthesis of (11)C‐Labelled Primary Benzamides via Intermediate [(11)C]Aroyl Dimethylaminopyridinium Salts
title_fullStr One‐Pot Synthesis of (11)C‐Labelled Primary Benzamides via Intermediate [(11)C]Aroyl Dimethylaminopyridinium Salts
title_full_unstemmed One‐Pot Synthesis of (11)C‐Labelled Primary Benzamides via Intermediate [(11)C]Aroyl Dimethylaminopyridinium Salts
title_short One‐Pot Synthesis of (11)C‐Labelled Primary Benzamides via Intermediate [(11)C]Aroyl Dimethylaminopyridinium Salts
title_sort one‐pot synthesis of (11)c‐labelled primary benzamides via intermediate [(11)c]aroyl dimethylaminopyridinium salts
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8251633/
https://www.ncbi.nlm.nih.gov/pubmed/33885193
http://dx.doi.org/10.1002/chem.202100544
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