Hideki Ishii

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Organization: National Institute of Radiological Sciences
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Co-reporter:Hideki Ishii, Katsuyuki Minegishi, Koutaro Nagatsu, Ming-Rong Zhang
Tetrahedron 2015 Volume 71(Issue 10) pp:1588-1596
Publication Date(Web):11 March 2015
DOI:10.1016/j.tet.2015.01.008
A new method has been developed for the Pd(0)-mediated [11C]carbonylation of aryl/heteroaryl boronic acid pinacol esters with [11C]carbon monoxide in the presence of p-benzoquinone and triphenylphosphine in a mixture of N,N-dimethylformamide (DMF) and methanol (MeOH) or just MeOH under ambient pressure at 65 °C. This method was used to convert a variety of different aryl/heteroaryl boronates to the corresponding [carbonyl-11C]esters with decay-corrected radiochemical yields in the range of 6–80%. Furthermore, some of these [carbonyl-11C]esters were treated with sodium hydroxide or aqueous ammonium to give the corresponding [carbonyl-11C]carboxylic acids and amides, respectively. This new method was also used to achieve the direct syntheses of [11C]aspirin using water or tetramethylammonium hydroxide as the nucleophile instead of MeOH in DMF.
tert-butyl 4-(4-bromothiazol-2-yl)piperazine-1-carboxylate
Carbamic acid, (3,4-dimethyl-5-isoxazolyl)-, 2,2,2-trichloroethyl ester
1-Piperazinecarboxamide,N-(3,4-dimethyl-5-isoxazolyl)-4-[4-(4-fluorophenyl)-2-thiazolyl]-
Carbon-11C monoxide(7CI,8CI,9CI)
AMMONIA; [(1R,2S,3R,4R,5S,6S)-2,3-DIHYDROXY-4,5,6-TRIPHOSPHONOOXY-CYCLOHEXYL] DIHYDROGEN PHOSPHATE
3-Quinolinecarboxamide