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Iodine(III)-mediated radiofluorination

A technology of fluoride and iodonium, applied in the field of iodonium ylide compounds, to achieve the effects of easy refining, excellent regioselectivity, and easy implementation

Active Publication Date: 2017-02-22
THE GENERAL HOSPITAL CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, using 18 F-Fluoride labeling of electron-rich (unactivated or deactivated) aromatics remains a long-standing and unmet challenge in routine PET radiopharmaceutical fabrication

Method used

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  • Iodine(III)-mediated radiofluorination
  • Iodine(III)-mediated radiofluorination
  • Iodine(III)-mediated radiofluorination

Examples

Experimental program
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preparation example Construction

[0333] The preparation of the compounds of the present invention may involve the protection and deprotection of various chemical groups. One skilled in the art can readily determine the need for protection and deprotection and the selection of appropriate protecting groups. The chemistry of protecting groups is described, for example, in Kocienski, Protecting Groups, (Thieme, 2007); Robertson, Protecting Group Chemistry, (Oxford University Press, 2000); Smith et al., March's Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 6 th Ed. (Wiley, 2007); Peturssion et al., "Protecting Groups in Carbohydrate Chemistry," J. Chem. Educ., 1997, 74(11), 1297; and Wuts et al., Protective Groups in Organic Synthesis, 4th Ed. , (Wiley, 2006).

[0334] The reaction can be monitored according to any suitable method known in the art. For example, product formation can be monitored by spectroscopic means, such as nuclear magnetic resonance spectroscopy (e.g., 1 H or 13 C), i...

Embodiment 1-27

[0593] Examples 1-27 were prepared according to General Method 8.

Embodiment 1

[0595] 1,3-Dimethylpyrimidine-2,4,6(1H,3H,5H)-trione-5-[1,1’-biphenyl-4-iodonium]ylide (8a)

[0596]

[0597] Yield: 32%, colorless solid. 1 H NMR (300MHz, CDCl 3 ): δ7.97 (d, J = 8.5Hz, 2H), 7.61 (d, J = 8.5Hz, 2H), 7.42–7.52 (m, 5H), 3.37 (s, 6H) ppm. 13 C NMR (75MHz, CDCl 3 ): δ161.1, 152.5, 145.2, 138.2, 137.3, 133.8, 130.1, 128.7, 126.8, 111.6, 68.3, 28.8ppm. HRMS(m / z): For C 18 h 16 IN 2 o 3 [M+H] of + Calculated, 435.0206; found 435.0192.

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Abstract

The invention relates to iodine(III)-mediated radiofluorination. According to the invention, a process for fluorination of aromatic compounds employing iodonium ylides and applicable to radiofluorination using 18F is described. Processes, intermediates, reagents and radiolabelled compounds are described.

Description

[0001] Corresponding application cross-referenced [0002] This application claims priority to US Provisional Application No. 61 / 949,302, filed March 7, 2014, the entire disclosure of which is incorporated herein by reference. technical field [0003] This invention relates to iodonium ylide compounds, and more particularly to iodonium ylide compounds useful for promoting radiofluorination reactions. Background technique [0004] Historically, the short-lived radionuclide fluorine-18 ( 18 F; t 1 / 2 = 109.7 minutes) to challenge the formation of aromatic C-F bonds. [0005] Fluorine-18-labeled compounds and radiopharmaceuticals are the backbone of functional molecular imaging by positron emission tomography (PET) for a wide range of applications including clinical diagnostics and drug discovery. Therefore, new markers for probing biological processes and targets in vivo 18 There is a rapidly growing demand for reagents of F. [0006] In a low-energy (10-16MeV) medical cyc...

Claims

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Application Information

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IPC IPC(8): C07D319/04
CPCC07B2200/05C07J1/0059C07J51/00C07B59/00C07D239/553C07D319/06C07D319/08C07D405/12C07J17/00C07D213/57C07B59/002
Inventor N·沃斯德夫B·H·罗特斯汀N·A·斯蒂芬森H·梁
Owner THE GENERAL HOSPITAL CORP
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