87956-06-7

Upstream product

• 17983-61-8 4-(trimethylsilyl)acetophenone 
• 171364-81-1 1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethanone 
• 13329-40-3 4-Iodoacetophenone 
• 149104-90-5 4-acetylphenylboronic acid 
• 1206189-55-0 4-acetyliodylbenzene 
• 867060-56-8 4-(carboxymethylphenyl)-4-(methoxyphenyl)iodonium trifluoroacetate 
• 100-19-6 (4-nitrophenyl)ethanone 

Downstream Products

• 112368-54-4 2-bromo-4'-[⁽¹⁸⁾F]-fluoroacetophenone 

Relevant academic research and scientific papers

Chemoselective Radiosyntheses of Electron-Rich [18F]Fluoroarenes from Aryl(2,4,6-trimethoxyphenyl)iodonium Tosylates

Hypervalent diaryliodonium salts have been used to produce various [18F]fluoroarenes. The iodonium salt approach as a labeling precursor has been established to equally afford complex 18F-fluorinated molecules. Because of the inheren

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

Catalyst-Free Aromatic Radiofluorination via Oxidized Iodoarene Precursors

Oxidized iodoarenes (OIAs), prepared via mCPBA-mediated oxidation, have been demonstrated as versatile precursors for the synthesis of [18F]fluoroarenes in the absence of catalysts. OIAs have been identified as intermediates in single-pot syntheses of iodonium salts and ylides but have never been recognized as radiofluorination precursors. Here, the isolated OIAs were used without any catalysts to produce functionalized [18F]fluoroarenes, regardless of the electronic nature of the arenes. This method was also applied to the production of radiolabeling synthons for use as aromatic 18F-labeled building blocks.

Synthesis of [18F]Arenes via the Copper-Mediated [18F]Fluorination of Boronic Acids

A copper-mediated radiofluorination of aryl- and vinylboronic acids with K18F is described. This method exhibits high functional group tolerance and is effective for the radiofluorination of a range of electron-deficient, -neutral, and -rich aryl-, heteroaryl-, and vinylboronic acids. This method has been applied to the synthesis of [18F]FPEB, a PET radiotracer for quantifying metabotropic glutamate 5 receptors.

A general copper-mediated nucleophilic 18F fluorination of arenes

Molecules labeled with fluorine-18 are used as radiotracers for positron emission tomography. An important challenge is the labeling of arenes not amenable to aromatic nucleophilic substitution (SNAr) with [ 18F]F-. In the

NUCLEOPHILIC FLUORINATION OF AROMATIC COMPOUNDS

Iodylbenzene derivatives substituted with electron donating as well as electron withdrawing groups on the aromatic ring are used as precursors in aromatic nucleophilic substitution reactions. The iodyl group (IO2) is regiospecifically substituted by nucleophilic fluoride to provide the corresponding fluoroaryl derivatives. No-carrier-added [F-18] fluoride ion derived from anhydrous [F- 18]KF/Kryptofix, [F-18]CsF or a quaternary ammonium fluoride (e.g., Me4NF, Et4NF, n-Bu4NF, (PhCH2)4NF) exclusively substitutes the iodyl moiety in these derivatives and provides high specific activity F- 18 labeled fluoroaryl analogs. Iodyl derivatives of a benzothiazole analog and 6-iodyl-L-dopa derivatives have been synthesized as precursors and have been used in the preparation of no-carrier-added [F-18]fluorobenzothiazole as well as 6-[F-18]fluoro-L-dopa.

Synthesis, radiofluorination and first evaluation of (±)-[ 18F]MDL 100907 as serotonin 5-HT2A receptor antagonist for PET

In some psychiatric disorders 5-HT2A receptors play an important role. In order to investigate those in vivo there is an increasing interest in obtaining a metabolically stable, subtype selective and high affinity radioligand for receptor binding studies using positron emission tomography (PET). Combining the excellent in vivo properties of [11C]MDL 100907 for PET imaging of 5-HT2A receptors and the more suitable half-life of fluorine-18, MDL 100907 was radiofluorinated in four steps using 1-(2-bromoethyl)-4-[18F]fluorobenzene as a secondary labelling precursor. The complex reaction required an overall reaction time of 140 min and (±)-[18F]MDL 100907 was obtained with a specific activity of at least 30 GBq/μmol (EOS) and an overall radiochemical yield of 1-2%. In order to verify its binding to 5-HT2A receptors, in vitro rat brain autoradiography was conducted showing the typical distribution of 5-HT 2A receptors and a very low non-specific binding of about 6% in frontal cortex, using ketanserin or spiperone for blocking. Thus, [18F]MDL 100907 appears to be a promising new 5-HT2A PET ligand. Copyright

FLUORIDATION METHOD

A method for the fluoridation of an iodonium salt with a fluoride ion source which can be carried out in an aqueous reaction solvent.

Fluorine-18-Labeled Progestin Ketals: Synthesis and Target Tissue Uptake Selectivity of Potential Imaging Agents for Receptor-Positive Breast Tumors

We have studied two new fluorine-substituted progestins as potential imaging agents for progesterone-receptor-positive human breast tumors. The steroids are 16α,17α-fluoroacetophenone ketals of 16α,17α-dihydroxyprogesterone and 16α,17α,21-trihydroxy-19-norprogesterone. Synthesis of the latter compound in seven steps from 19-norandrost-4-ene-3,17-dione is reported. Both compounds demonstrate high affinity for the progesterone receptor (PgR) (52.5 and 240percent, respectively, relative to R5020 = 100). The syntheses were adapted to 18F-labeling with 4'--fluoroacetophenone, prepared from 4'-nitroacetophenone by nucleophilic substitution with K18F/Kryptofix. Considerable adjustment of reaction conditions was required to effect ketalization using tracer quantities of the ketone. In tissue distribution studies in estrogen-primed immature female rats, both ketals showed selective uterine uptake, which was blocked by coinjection of a saturating dose of the unlabeled progestin ORG 2058. Additionally, metabolic stability of the radiolabel was indicated by the low radioactivity levels seen in bone. Both compounds showed relatively high uptake in fat, in accord with their relative lipophilicities demonstrated by HPLC-derived octanol-water partition coefficients. The selective uterine uptake and metabolic stability of these compounds suggests that this class of PgR ligands might be promising for the selective imaging of receptor-positive tumors if derivatives of reduced lipophilicity can be prepared.

NUCLEOPHILIC AROMATIC SUBSTITUTION OF ACTIVATED CATIONIC GROUPS BY 18F-LABELED FLUORIDE. A USEFUL ROUTE TO NO-CARRIER-ADDED (NCA) 18F-LABELED ARYL FLUORIDES

A method is described for the rapid preparation of no-carrier-added (NCA) 18F-labeled aryl fluorides by treatment of the corresponding aryltrimethylammonium perchlorates with 18F-labeled fluoride in DMSO.The basic features of the 18F-for-+NMe3 displacement process are evaluated as a function of the experimental variables and compared with related substitution routes to NCA 18F-labeled aryl fluorides.The relative nucleofugicity of the ammonium group in the nucleophilic substitution reactions surpasses that of the best neutral leaving groups, including NO2 and F itself.In contrast, radiofluoride incorporation into aromatic rings via other cationic substrates, such as aryldimethylsulfonium perchlorates, is prevented by the fast methyl group transfer from the starting compound to the nucleophiles present.The use of the ammonium function as a leaving group in nucleophilic substitutions by 18F- may give access to the rapid preparation of novel NCA 18F-radiopharmaceuticals by facilitating the synthesis and the purification of their labeled precursors.