93826-89-2

Upstream product

• 134952-89-9 (3,4-dimethoxyphenyl)trimethylstannane 
• 5460-32-2 1-iodo-3,4-dimethoxybenzene 
• 86487-18-5 tri-n-butyl(3,4-dimethoxyphenyl)stannane 
• 91-16-7 1,2-dimethoxybenzene 
• 365564-10-9 2-(3,4-dimethoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 122775-35-3 3,4-Dimethoxyphenylboronic acid 
• 398-62-9 4-fluoroveratrole 

Relevant academic research and scientific papers

Cu-Mediated Radiofluorination of Aryl Pinacolboronate Esters: Alcohols as Solvents with Application to 6-L-[18F]FDOPA Synthesis

Cu-mediated radiofluorination of arylboronic acid pinacol esters (ArylBPin) using Cu(OTf)2(Py)4 complex is a useful approach for the introduction of [18F]fluorine into non-activated arenes and heteroarenes. Owing to the co

Sequential Ir/Cu-Mediated Method for the Meta-Selective C-H Radiofluorination of (Hetero)Arenes

This article describes a sequential Ir/Cu-mediated process for the meta-selective C-H radiofluorination of (hetero)arene substrates. In the first step, Ir-catalyzed C(sp2)-H borylation affords (hetero)aryl pinacolboronate (BPin) esters. The intermediate organoboronates are then directly subjected to copper-mediated radiofluorination with [18F]tetrabutylammonium fluoride to afford fluorine-18 labeled (hetero)arenes in high radiochemical yield and radiochemical purity. This entire process is performed on a benchtop without Schlenk or glovebox techniques and circumvents the need to isolate (hetero)aryl boronate esters. The reaction was automated on a TracerLab FXFN module with 1,3-dimethoxybenzene and a meta-tyrosine derivative. The products, [18F]1-fluoro-3,5-dimethoxybenzene and an 18F-labeled meta-tyrosine derivative, were obtained in 37 ± 5% isolated radiochemical yield and >99% radiochemical purity and 25% isolated radiochemical yield and 99% radiochemical purity, and 0.52 Ci/μmol (19.24 GBq/μmol) molar activity (Am), respectively.

MCR scaffolds get hotter with 18F-Labeling

Imaging techniques, such as positron emission tomography (PET), represent great progress in the clinical development of drugs and diagnostics. However, the efficient and timely synthesis of appropriately labeled compounds is a largely unsolved problem. Nu

Copper-Mediated Radiofluorination of Aryl Pinacolboronate Esters: A Straightforward Protocol by Using Pyridinium Sulfonates

Radiofluorination of arylboronic acids pinacol esters (arylBPin) mediated by copper triflate pyridine complex is one of the more promising synthetic approaches for the direct introduction of nucleophilic [18F]fluoride into non-activated arenes

An azeotropic drying-free approach for copper-mediated radiofluorination without addition of base

Copper-mediated radiofluorination provides a quick and versatile approach for 18F-labeling of arenes and heteroarenes. However, this method is known to be base sensitive, which has been a barrier for preparative scale radiosynthesis. In this re

Alcohol-Enhanced Cu-Mediated Radiofluorination

The potential of many 18F-labeled (hetero)aromatics for applications in positron emission tomography remains underexplored because convenient procedures for their radiosynthesis are lacking. Consequently, simple methods to prepare radiofluorinated (hetero)arenes are highly sought after. Herein, we report the beneficial effect of primary and secondary alcohols on Cu-mediated 18F-labeling. This observation contradicts the assumption that such alcohols are inappropriate solvents for aromatic fluorination. Therefore, we developed a protocol for rapid radiolabeling of an extraordinarily broad scope of boronic and stannyl substrates under general reaction conditions. Notably, radiofluorinated indoles, phenols, and anilines were synthesized directly from the corresponding unprotected precursors. Furthermore, the novel method enabled the preparation of radiofluorinated tryptophans, [18F]F-DPA, [18F]DAA1106, 6-[18F]FDA, and 6-[18F]FDOPA.

COPPER CATALYZED [18F]FLUORINATION OF IODONIUM SALTS

Copper-catalyzed radiofluorination of iodonium salts, iodonium salts, and compounds obtained by copper-catalyzed radiofluorination of iodonium salts are disclosed. Diagnostic and therapeutic methods involving such compounds also are disclosed.

Copper-Mediated Radiofluorination of Arylstannanes with [18F]KF

A copper-mediated nucleophilic radiofluorination of aryl- and vinylstannanes with [18F]KF is described. This method is fast, uses commercially available reagents, and is compatible with both electron-rich and electron-deficient arene substrates. This method has been applied to the manual synthesis of a variety of clinically relevant radiotracers including protected [18F]F-phenylalanine and [18F]F-DOPA. In addition, an automated synthesis of [18F]MPPF is demonstrated that delivers a clinically validated dose of 200 ± 20 mCi with a high specific activity of 2400 ± 900 Ci/mmol.

Enhanced copper-mediated 18F-fluorination of aryl boronic esters provides eight radiotracers for PET applications

[18F]FMTEB, [18F]FPEB, [18F]flumazenil, [18F]DAA1106, [18F]MFBG, [18F]FDOPA, [18F]FMT and [18F]FDA are prepared from the corresponding arylboronic esters and [18

FLUORINATION METHOD

The present invention relates to a process for producing an organic compound comprising an 18F atom. The compounds comprising an 18F can be useful as PET ligands for use in diagnostics and/or scanning. The process of the invention comprises treating an organoboron compound, which organoboron compound comprises a boron atom bonded to an sp2 hybridised carbon atom, with (i) 18F – and (ii) a copper compound. The invention also provides the use of an organoboron compound, which organoboron compound comprises a boron atom bonded to an sp2 hybridised carbon atom, in a process for producing an organic compound comprising an 18F atom, which process comprises treating the organoboron compound with (i) 18F – and (ii) a copper compound. The invention also provides a compound of formula (XXXVII): wherein: each PGA is independently H or an alcohol protecting group; PGB is H or a carboxylic acid protecting group; each PGC is independently an amine protecting group; Z is a group selected from a boronic ester group, a boronic acid group, a borate group, and a trifluoroborate group; and a is an integer from 0 to 4.