000866645 001__ 866645
000866645 005__ 20210130003552.0
000866645 0247_ $$2Handle$$a2128/23522
000866645 037__ $$aFZJ-2019-05724
000866645 1001_ $$0P:(DE-Juel1)166553$$aOmrane, Aymen$$b0
000866645 1112_ $$aThe 23rd International Symposium on Radiopharmaceutical Sciences$$cBeijing$$d2019-05-26 - 2019-05-31$$wChina
000866645 245__ $$a2‐[18F]Fluoro‐5‐iodopyridine ([18F]FIPy): A novel reactive prosthetic group for the fast site specific radiolabeling via Pd‐catalyzed cross coupling reactions
000866645 260__ $$c2019
000866645 3367_ $$033$$2EndNote$$aConference Paper
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000866645 3367_ $$0PUB:(DE-HGF)6$$2PUB:(DE-HGF)$$aConference Presentation$$bconf$$mconf$$s1575375828_15199$$xAfter Call
000866645 520__ $$aAim: Numerous Pd‐catalyzed cross‐couplings like Sonogashira, Suzuki‐Miyaura, Heck, and Stille reactions proved to be valuable tools for the site specific labeling of biopolymers. The aim of this work was the study of Pd‐catalyzed cross coupling reactions using [18F]FIPy as radiolabeled synthon and 2,2′‐(1,2‐phenylene)‐bis‐(4,4‐dimethyl‐4,5‐dihydrooxazole)‐N,N′‐palladium dichloride (Pd‐BOX‐1) as catalyst. Pd‐BOX‐1 demonstrated exceptional air and moisture stability and excellent catalytic activity in aqueous reaction media. MethodsThe direct reaction of 2‐bromo‐5‐iodopyridine with DABCO followed by anion metathesis using TMSOTf afforded 1‐(5‐iodopyridin‐2‐yl)‐1,4‐diazabicyclo[2.2.2]octan‐1‐ium triflate (1) used as precursor for the preparation of [18F]FIPy. The latter was produced using the “minimalist” protocol. Accordingly, [18F]fluoride was eluted from a QMA cartridge with a solution of 1 in MeOH. MeOH was evaporated at 45°C (250 mbar) within 4 min, DMSO was added, and the resulting solution was heated affording [18F]FIPy, which after the purification by SPE was conjugated to different model compounds by different Pd‐catalyzed (1% of Pd‐BOX‐1) cross‐couplings using aqueous MeCN or DMF as reaction solvent within 10 min. Results18F– recovery from an anion exchange resin using 1 (3 mg) amounted >98%. Heating of the resulting [18F]fluoride onium salt in DMSO at 100°C for 15 min afforded [18F]FIPy in excellent radiochemical conversions (RCCs) of 91 ± 3%. [18F]FIPy was isolated in 61 ± 5% radiochemical yield (RCY) and excellent radiochemical purity (RCP) of >98%. The subsequent Cu and phosphine free Pd‐BOX‐1 catalyzed Sonogashira cross‐coupling with phenylacetylene afforded the corresponding conjugate in an excellent RCC of >89%. Furthermore, Suzuki‐Miyaura, Heck, and Stille reactions with 4‐methylphenyl boronic acid, methyl acrylate, and trimethyl (phenyl)tin, respectively, applied as model coupling partners furnished the corresponding radiofluorinated conjugates in RCCs of 85–98%. Conclusion[18F]FIPy is a valuable radiolabeled prosthetic group easily accessible using the “minimalist” approach. Various Pd‐BOX‐1‐catalyzed cross coupling reactions with [18F]FIPy is a versatile procedure for a fast, high‐yielding, and site specific radiolabeling under relatively mild conditions.
000866645 536__ $$0G:(DE-HGF)POF3-573$$a573 - Neuroimaging (POF3-573)$$cPOF3-573$$fPOF III$$x0
000866645 7001_ $$0P:(DE-Juel1)176188$$aZlatopolskiy, Boris$$b1$$ufzj
000866645 7001_ $$0P:(DE-Juel1)166419$$aNeumaier, Bernd$$b2$$eCorresponding author$$ufzj
000866645 8564_ $$uhttps://juser.fz-juelich.de/record/866645/files/Abstract%20ISRS%202019%20Omrane.pdf$$yOpenAccess
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000866645 9101_ $$0I:(DE-588b)5008462-8$$6P:(DE-Juel1)176188$$aForschungszentrum Jülich$$b1$$kFZJ
000866645 9101_ $$0I:(DE-588b)5008462-8$$6P:(DE-Juel1)166419$$aForschungszentrum Jülich$$b2$$kFZJ
000866645 9131_ $$0G:(DE-HGF)POF3-573$$1G:(DE-HGF)POF3-570$$2G:(DE-HGF)POF3-500$$3G:(DE-HGF)POF3$$4G:(DE-HGF)POF$$aDE-HGF$$bKey Technologies$$lDecoding the Human Brain$$vNeuroimaging$$x0
000866645 9141_ $$y2019
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000866645 9201_ $$0I:(DE-Juel1)INM-5-20090406$$kINM-5$$lNuklearchemie$$x0
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