Synthesis of 2-(Chlorodifluoromethyl)indoles for Nucleophilic Halogen Exchange with [18F]Fluoride

Leonard Bock; Stefanie K. Schultheiß; Simone Maschauer; Roman Lasch; Susanne Gradl; Olaf Prante; Samir Z. Zard; Markus R. Heinrich

doi:10.1002/ejoc.202100937

Synthesis of 2-(Chlorodifluoromethyl)indoles for Nucleophilic Halogen Exchange with [¹⁸F]Fluoride

Leonard Bock
, Stefanie K. Schultheiß
, Simone Maschauer
, Roman Lasch
, Susanne Gradl
, Olaf Prante
, Samir Z. Zard
, Markus R. Heinrich

Friedrich-Alexander University (FAU) Erlangen-Nürnberg and Universitätsklinikum Erlangen
Laboratoire de Synthèse Organique

Résultats de recherche: Contribution à un journal › Article › Revue par des pairs

7 Citations (Scopus)

Résumé

The synthesis of 2-[¹⁸F]trifluoromethylated indoles from the corresponding chlorodifluoromethyl precursors was found to proceed under milder conditions when compared to known metal-free nucleophilic exchange reactions with [¹⁸F]fluoride on chlorodifluoro-methyl arenes. A key element in the reaction course is – most likely – a favorable elimination-addition mechanism on the 2-methyl position of the indole. Given the increasing interest in ¹⁸F-labelled compounds, this single step labeling methodology nicely complements the so far existing routes to 2-[¹⁸F]trifluoromethylated indoles.

langue originale	Anglais
Pages (de - à)	6258-6262
Nombre de pages	5
journal	European Journal of Organic Chemistry
Volume	2021
Numéro de publication	46
Les DOIs	https://doi.org/10.1002/ejoc.202100937
état	Publié - 14 déc. 2021
Modification externe	Oui

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10.1002/ejoc.202100937

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@article{8b019da1be184e529e48482c700e3626,

title = "Synthesis of 2-(Chlorodifluoromethyl)indoles for Nucleophilic Halogen Exchange with [18F]Fluoride",

abstract = "The synthesis of 2-[18F]trifluoromethylated indoles from the corresponding chlorodifluoromethyl precursors was found to proceed under milder conditions when compared to known metal-free nucleophilic exchange reactions with [18F]fluoride on chlorodifluoro-methyl arenes. A key element in the reaction course is – most likely – a favorable elimination-addition mechanism on the 2-methyl position of the indole. Given the increasing interest in 18F-labelled compounds, this single step labeling methodology nicely complements the so far existing routes to 2-[18F]trifluoromethylated indoles.",

keywords = "Fluorine, Indoles, Nucleophilic substitution, Radical reactions, Radiochemistry",

author = "Leonard Bock and Schulthei{\ss}, \{Stefanie K.\} and Simone Maschauer and Roman Lasch and Susanne Gradl and Olaf Prante and Zard, \{Samir Z.\} and Heinrich, \{Markus R.\}",

note = "Publisher Copyright: {\textcopyright} 2021 The Authors. European Journal of Organic Chemistry published by Wiley-VCH GmbH",

year = "2021",

month = dec,

day = "14",

doi = "10.1002/ejoc.202100937",

language = "English",

volume = "2021",

pages = "6258--6262",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

publisher = "Wiley-VCH Verlag",

number = "46",

}

TY - JOUR

T1 - Synthesis of 2-(Chlorodifluoromethyl)indoles for Nucleophilic Halogen Exchange with [18F]Fluoride

AU - Bock, Leonard

AU - Schultheiß, Stefanie K.

AU - Maschauer, Simone

AU - Lasch, Roman

AU - Gradl, Susanne

AU - Prante, Olaf

AU - Zard, Samir Z.

AU - Heinrich, Markus R.

PY - 2021/12/14

Y1 - 2021/12/14

N2 - The synthesis of 2-[18F]trifluoromethylated indoles from the corresponding chlorodifluoromethyl precursors was found to proceed under milder conditions when compared to known metal-free nucleophilic exchange reactions with [18F]fluoride on chlorodifluoro-methyl arenes. A key element in the reaction course is – most likely – a favorable elimination-addition mechanism on the 2-methyl position of the indole. Given the increasing interest in 18F-labelled compounds, this single step labeling methodology nicely complements the so far existing routes to 2-[18F]trifluoromethylated indoles.

AB - The synthesis of 2-[18F]trifluoromethylated indoles from the corresponding chlorodifluoromethyl precursors was found to proceed under milder conditions when compared to known metal-free nucleophilic exchange reactions with [18F]fluoride on chlorodifluoro-methyl arenes. A key element in the reaction course is – most likely – a favorable elimination-addition mechanism on the 2-methyl position of the indole. Given the increasing interest in 18F-labelled compounds, this single step labeling methodology nicely complements the so far existing routes to 2-[18F]trifluoromethylated indoles.

KW - Fluorine

KW - Indoles

KW - Nucleophilic substitution

KW - Radical reactions

KW - Radiochemistry

U2 - 10.1002/ejoc.202100937

DO - 10.1002/ejoc.202100937

M3 - Article

AN - SCOPUS:85121107150

SN - 1434-193X

VL - 2021

SP - 6258

EP - 6262

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 46

ER -

Synthesis of 2-(Chlorodifluoromethyl)indoles for Nucleophilic Halogen Exchange with [18F]Fluoride

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Synthesis of 2-(Chlorodifluoromethyl)indoles for Nucleophilic Halogen Exchange with [¹⁸F]Fluoride