60345-74-6Relevant academic research and scientific papers
Synthesis and biodistribution of [11C]R116301, a promising PET ligand for central NK1 receptors
Van Der Mey,Janssen,Janssens,Jurzak,Langlois,Sommen,Verreet,Windhorst,Leysen,Herscheid
, p. 1579 - 1586 (2005)
N1-(2,6-Dimethylphenyl)-2-(4-{(2R,4S)-2-benzyl-1-[3,5-di(trifluoromethyl) [carbonyl-11C]benzoyl]hexahydro-4-pyridinyl}piperazino)acetamide ([11C]R116301) was prepared and evaluated as a potential positron emission tomography (PET) li
Carbon-11 carboxylation of trialkoxysilane and trimethylsilane derivatives using [11C]CO2
Bongarzone, Salvatore,Fontana, Igor Camargo,Gee, Antony D.,Luzi, Federico,Raucci, Nicola
, p. 4668 - 4671 (2020)
A novel carboxylation radiosynthesis methodology is described starting from cyclotron-produced [11C]CO2 and fluoride-activated silane derivatives. Six carbon-11 labelled carboxylic acids were obtained from their corresponding trimethylsilyl and trialkoxysilyl precursors in a one-pot labelling methodology. The radiochemical yields ranged from 19% to 93% within 12 minutes post [11C]CO2 delivery with a trapping efficiency of 21-89%.
“In-loop” carbonylation—A simplified method for carbon-11 labelling of drugs and radioligands
Ferrat, Mélodie,Dahl, Kenneth,Halldin, Christer,Schou, Magnus
, p. 100 - 107 (2020/02/04)
Transition-metal mediated carbonylation with 11C-labelled carbon monoxide ([11C]CO) is a versatile method for introducing 11C (t1/2 = 20.3 min) into drugs and radioligands for subsequent use in positron emission tomography (PET). The aim of the current study was to perform the 11C-carbonylation reaction on the interior surface of a stainless-steel loop used for high performance liquid chromatography (HPLC). In the experimental setup, cyclotron produced 11C-labelled carbon dioxide ([11C]CO2) was converted to [11C]CO by reduction over heated Molybdenum and swept into an HPLC loop pre-charged with the appropriate reaction mixture. Following a 5 min reaction, the radiochemical purity (RCP) and the trapping efficiency (TE) of the reaction mixture was determined. After optimization, [11C]N-Benzylbenzamide was obtained in quantitative radiochemical yield (RCY) following a 5 min reaction at room temperature. The methodology was further applied to label [11C]benzoic acid (RCP≥99%, TE>91%), [11C]methyl benzoate (RCP≥99%, TE>93%) and [11C]phthalide (RCP≥99%, TE>88%). A set of pharmaceuticals was finally radiolabelled using non-optimized conditions. Excellent yields were obtained for the histamine-3 receptor radioligand [11C]AZ13198083, the oncology drug [11C]olaparib and the dopamine D2 receptor radioligand [11C]raclopride, whereas a moderate yield was observed for the high-affinity dopamine D2 receptor radioligand [11C]FLB457. The presented “in-loop” process proved efficient for diverse 11C-carbonylations, providing [11C]amides, [11C]esters and [11C]carboxylic acids in moderate to excellent RCYs. Based on the advantages associated with performing the radiolabelling step as an integrated part of the purification system, this methodology may become a valuable addition to the toolbox of methodologies used for 11C-carbonylation of drugs and radioligands for PET.
Pd(0)-Mediated 11C-Carbonylation of Aryl(mesityl)iodonium Salts as a Route to [11C]Arylcarboxylic Acids and Derivatives
Altomonte, Stefano,Telu, Sanjay,Lu, Shuiyu,Pike, Victor W.
, p. 11925 - 11932 (2017/11/24)
Pd(0)-mediated 11C-carbonylation of aryl(mesityl)iodonium salts followed by suitable quench provides a rapid room-temperature two-pot procedure for labeling arylcarboxylic acids and amide derivatives with the short-lived positron emitter carbon
An evaluation of a high-pressure 11CO carbonylation apparatus
Dahl, Kenneth,Itsenko, Oleksiy,Rahman, Obaidur,Ulin, Johan,Sj?berg, Carl-Olof,Sandblom, Peter,Larsson, Lars-Anders,Schou, Magnus,Halldin, Christer
, p. 220 - 225 (2015/05/20)
[11C]Carbon monoxide (11CO) is a versatile building block for the synthesis of Positron Emission Tomography (PET) radioligands. However, the difficulty of trapping 11CO in a small solvent volume has limited its utility. We
Improved synthesis and application of [11C]benzyl iodide in positron emission tomography radiotracer production
Peko?ak, Aleksandra,Filp, Ulrike,Rotteveel, Lonneke,Poot, Alex J.,Windhorst, Albert D.
, p. 342 - 348 (2015/08/03)
Positron emission tomography has increased the demand for new carbon-11 radiolabeled tracers and building blocks. A promising radiolabeling synthon is [11C]benzyl iodide ([11C]BnI), because the benzyl group is a widely present functi
Improved yields for the palladium-mediated 11C-carbonylation reaction using microwave technology
Dahl, Kenneth,Schou, Magnus,Rahman, Obaidur,Halldin, Christer
supporting information, p. 307 - 310 (2014/01/23)
Microwave heating technology was applied for the palladium-mediated 11C-carbonylation of aryl halides and triflates at ambient pressure using xantphos as supporting ligand. Improved yields were observed for the 11C-aminocarbonylation of electron-deficient aryl halides in comparison to thermal heating and the approach even allowed the use of an aryl chloride as substrate. The scope of this reaction was further extended to 11C-labeled aryl acid and two 11C-labeled aryl esters. Microwave heating was applied for the palladium-mediated 11C- carbonylation of aryl halides and triflates using xantphos as supporting ligand. Improved yields were observed for the 11C-aminocarbonylation of electron-deficient aryl halides in comparison to thermal heating and even allowed the use of an aryl chloride as substrate. A 11C-labeled aryl acid and two 11C-labeled aryl esters were also obtained. Copyright
Improved Yields for the Palladium-Mediated 11C-Carbonylation Reaction Using Microwave Technology
Dahl, Kenneth,Schou, Magnus,Rahman, Obaidur,Halldin, Christer
supporting information, p. 307 - 310 (2015/10/05)
Microwave heating technology was applied for the palladium-mediated 11C-carbonylation of aryl halides and triflates at ambient pressure using xantphos as supporting ligand. Improved yields were observed for the 11C-aminocarbonylation of electron-deficient aryl halides in comparison to thermal heating and the approach even allowed the use of an aryl chloride as substrate. The scope of this reaction was further extended to 11C-labeled aryl acid and two 11C-labeled aryl esters. Microwave heating was applied for the palladium-mediated 11C-carbonylation of aryl halides and triflates using xantphos as supporting ligand. Improved yields were observed for the 11C-aminocarbonylation of electron-deficient aryl halides in comparison to thermal heating and even allowed the use of an aryl chloride as substrate. A 11C-labeled aryl acid and two 11C-labeled aryl esters were also obtained.
Palladium-mediated [11C]carbonylation at atmospheric pressure: A general method using xantphos as supporting ligand
Dahl, Kenneth,Schou, Magnus,Amini, Nahid,Halldin, Christer
supporting information, p. 1228 - 1231 (2013/03/28)
The palladium-catalyzed [11C]carbonylation of aryl halides and triflates was achieved at atmospheric pressure by employing xantphos as the supporting ligand. Aryl halides were converted into their corresponding [ 11C]amides in good t
N-heterocyclic carbenes as ligands in palladium-mediated [ 11C]radiolabelling of [11C]amides for positron emission tomography
Jennings, Lucy E.,Kealey, Steven,Miller, Philip W.,Gee, Antony D.,Long, Nicholas J.
experimental part, p. 135 - 139 (2011/10/12)
A model palladium-mediated carbonylation reaction synthesizing N-benzylbenzamide from iodobenzene and benzylamine was used to investigate the potential of four N-heterocyclic carbenes (N,N′-bis(diisopropylphenyl)-4, 5-dihydroimidazolinium chloride (I), N,N′-bis(1-mesityl)-4,5- dihydroimidazolinium chloride (II), N,N′-bis(1-mesityl)imidazolium chloride (III) and N,N′-bis(1-adamantyl)imidazolium chloride (IV)) to act as supporting ligands in combination with Pd2(dba)3. Their activities were compared with other Pd-diphosphine complexes after reaction times of 10 and 120 min. Pd2(dba)3 and III were the best performing after 10 min reaction (20%) and was used to synthesize radiolabelled [11C]N-benzylbenzamide in good radiochemical yield (55%) and excellent radiochemical purity (99%). A Cu(Tp*) complex was used to trap the typically unreactive and insoluble [11C]CO which was then released and reacted via the Pd-mediated carbonylation process. Potentially useful side products [11C]N,N′-dibenzylurea and [ 11C]benzoic acid were also observed. Increased amounts of [ 11C]N,N′-dibenzylurea were yielded when PdCl2 was the Pd precursor. Reduced yields of [11C]benzoic acid and therefore improved RCP were seen for III/Pd2(dba)3 over commonly used dppp/Pd2(dba)3 making it more favourable in this case. Copyright
