Improved Methods for the Synthesis of [ω-<sup>11</sup>C]Palmitic Acid

Hostetler, Eric D.; Fallis, Stephen; McCarthy, Timothy J.; Welch, Michael J.; Katzenellenbogen, John A.

doi:10.1021/jo9718657

Cited by 46 publications

(29 citation statements)

References 11 publications

(36 reference statements)

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“…The symmetrical 4,4 0 -diiododiphenyliodonium salts 2, 3 and 5 were used as precursors for radiofluorinations with The summary clearly shows the important influence of temperature and solvent on the radiochemical yield, showing a maximum at 1408C with DMF as the solvent (runs [4][5][6][7]10,13). This finding agrees with the results obtained by Gail et al 16 since high reaction temperatures seem to be essential for an efficient thermal decomposition of diaryliodonium salts in a highly polar aprotic solvent.…”

Section: Synthesis Of 4-[ 18 F]fluoroiodobenzenementioning

confidence: 99%

Synthesis of 4‐[¹⁸F]fluoroiodobenzene and its application in sonogashira cross‐coupling reactions

Wüst

Knieß

2003

Labelled Comp Radiopharmac

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The first application of a Sonogashira cross‐coupling reaction in 18F chemistry has been developed. The reaction was exemplified by the cross‐coupling of terminal alkynes (ethynylcyclopentyl carbinol 6, 17α‐ethynyl‐3,17β‐estradiol 7 and 17α‐ethynyl‐3‐methoxy‐3,17β‐estradiol 8) with 4‐[18F]fluoroiodobenzene. 4,4′‐Diiododiaryliodonium salts were used as precursors for the synthesis of 4‐[18F]fluoroiodobenzene, enabling the convenient access to 4‐[18F]fluoroiodobenzene in 13–70% yield using conventional heating or microwave activation. The Sonogashira cross‐coupling of 4‐[18F]fluoroiodobenzene with terminal alkynes gave the corresponding 4‐[18F]fluorophenylethynyl‐substituted compounds [18F]‐9, [18F]‐10 and [18F]‐13 in yields up to 88% within 20 min of starting from 4‐[18F]fluoroiodobenzene. Copyright © 2003 John Wiley & Sons, Ltd.

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Section: Synthesis Of 4-[ 18 F]fluoroiodobenzenementioning

confidence: 99%

Synthesis of 4‐[¹⁸F]fluoroiodobenzene and its application in sonogashira cross‐coupling reactions

Wüst

Knieß

2003

Labelled Comp Radiopharmac

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“…After allowance for decay, an 83% yield of [C-11]-iodomethane was obtained after 7 min. This process has been successfully applied 22 …”

Section: Preparation and Application Of [C-11]-methylating Agentsmentioning

confidence: 97%

Isotopic methylation

Bolton

2001

Labelled Comp Radiopharmac

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SummaryThis review reports recent methods by which organic compounds, and especially pharmaceuticals, have been isotopically labelled by the incorporation of carbon or hydrogen isotopes in methylation processes. Particular attention is paid to the incorporation of carbon-11; both the synthesis of such labelled methylating agents and applications of their use are discussed. The review has reported reagents and conditions by which a number of organic compounds have been obtained recently. It also assesses the limitations of reported methods and proposes some alternative techniques and innovations.The application of catalysts such as Ag + and conditions such as microwave irradiation to encourage these reactions are also included, with suggestions of other, potentially beneficial, ways to assist them. In many cases, the radio-chemical yield and purity of the labelled product are given along with an estimate of the total reaction time.

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“…Moreover, the Suzuki reaction has already proved to be a reliable and robust synthetic method in the synthesis of several 11 C-labelled compounds. 10,11 In this report, we describe the synthesis of various …”

Section: Introductionmentioning

confidence: 99%

Synthesis of18F-labelled biphenyls via SUZUKI cross-coupling with 4-[18F]fluoroiodobenzene

Steiniger

Wuest

2006

J Label Compd Radiopharm

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Improved Methods for the Synthesis of [ω-¹¹C]Palmitic Acid

Cited by 46 publications

References 11 publications

Synthesis of 4‐[¹⁸F]fluoroiodobenzene and its application in sonogashira cross‐coupling reactions

Synthesis of 4‐[¹⁸F]fluoroiodobenzene and its application in sonogashira cross‐coupling reactions

Isotopic methylation

Synthesis of18F-labelled biphenyls via SUZUKI cross-coupling with 4-[18F]fluoroiodobenzene

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Improved Methods for the Synthesis of [ω-11C]Palmitic Acid

Cited by 46 publications

References 11 publications

Synthesis of 4‐[18F]fluoroiodobenzene and its application in sonogashira cross‐coupling reactions

Synthesis of 4‐[18F]fluoroiodobenzene and its application in sonogashira cross‐coupling reactions

Isotopic methylation

Synthesis of18F-labelled biphenyls via SUZUKI cross-coupling with 4-[18F]fluoroiodobenzene

Contact Info

Product

Resources

About

Improved Methods for the Synthesis of [ω-¹¹C]Palmitic Acid

Synthesis of 4‐[¹⁸F]fluoroiodobenzene and its application in sonogashira cross‐coupling reactions

Synthesis of 4‐[¹⁸F]fluoroiodobenzene and its application in sonogashira cross‐coupling reactions