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Synthesis of Aryl [11C]/(13C)Carboxylic Acids using Aryl Triflates and [11C]/(13)Carbon Monoxide
Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry.
Manuscript (Other academic)
URN: urn:nbn:se:uu:diva-91586OAI: oai:DiVA.org:uu-91586DiVA: diva2:164366
Available from: 2004-04-13 Created: 2004-04-13 Last updated: 2010-01-13Bibliographically approved
In thesis
1. [11C]Carbon Monoxide and Aryl Triflates in Palladium-Mediated Carbonylation Reactions: Synthetic approaches to [11C]Carbonyl Compounds and [11C]Amines
Open this publication in new window or tab >>[11C]Carbon Monoxide and Aryl Triflates in Palladium-Mediated Carbonylation Reactions: Synthetic approaches to [11C]Carbonyl Compounds and [11C]Amines
2004 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

The usefulness of low concentrations (typically 10 to 100 µM) of [11C]carbon monoxide and aryl triflates as substrates in 11C-carbonylation using different nucleophiles in the presence of lithium bromide was investigated. The reactions were performed in a micro autoclave of 200 µL volume and catalysed (mediated) by palladium(0).

A peripheral type benzodiazepine receptor (PBR) ligand, 1-(2-chlorophenyl)-N-methyl-N-(1-methylpropyl)isoquinoline-3-carboxamide (PK11195) and its structural analogues including an irreversible ligand for PBR, some other amides, ketones and carboxylic acids, were all labelled with 11C using this approach. The [carbonyl-11C]PK11195, analogues and other amides were prepared from aryl triflates and amines, and the [carbonyl-11C]ketones were prepared from aryl triflates and organoboranes. In the synthesis of [carboxyl-11C]carboxylic acids, water was utilised as nucleophile. The decay-corrected radiochemical yields were 10 to 55% for [11C]PK11195 and analogues, 2 to 63% for other [11C]amides, 10 to 75% for [11C]ketones and 25 to 65% for [11C]carboxylic acids. The specific radioactivity of the labelled compounds was in the range of 150 to 900 GBq/µmol.

Some [11C]amines were prepared by a reductive amination of the corresponding [carbonyl-11C]ketones. These reactions were performed using different amines in the presence of TiCl4 and NaBH3CN. The radiochemical yields of the [11C]amines varied from 2 to 78% (determined by analytical HPLC).

In order to confirm the labelling position, synthesis of selected 13C-substituted compounds were performed. For each substance group/ synthesis method, a selected compound was synthesised using (13C)carbon monoxide and the 13C-substituted compound was then analysed by 13C NMR.

A synthetic route was developed for the preparation of 1-(2-chloro-phenyl)-isoquinolin-3-yl trifluoromethanesulfonate used as the precursor in the synthesis of [carbonyl-11C]PK11195 and analogues.

Place, publisher, year, edition, pages
Uppsala: Acta Universitatis Upsaliensis, 2004. 40 p.
Comprehensive Summaries of Uppsala Dissertations from the Faculty of Science and Technology, ISSN 1104-232X ; 960
Organic chemistry, [11C]Carbon monoxide, Aryl triflates, Carbonylation, Organisk kemi
National Category
Organic Chemistry
urn:nbn:se:uu:diva-4157 (URN)91-554-5930-7 (ISBN)
Public defence
2004-05-07, B41, BMC, Uppsala, 10:15
Available from: 2004-04-13 Created: 2004-04-13Bibliographically approved

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