Synthesis of [11C]Am80 via Novel Pd(0)-Mediated Rapid [11C]Carbonylation Using Arylboronate and [11C]Carbon Monoxide

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• 作者：Misato Takashima-Hirano ; Hideki Ishii ; Masaaki Suzuki
• 刊名：ACS Medicinal Chemistry Letters
• 出版年：2012
• 出版时间：October 11, 2012
• 年：2012
• 卷：3
• 期：10
• 页码：804-807
• 全文大小：220K
• 年卷期：v.3,no.10(October 11, 2012)
• ISSN：1948-5875

文摘

¹¹C-labeled methylbenzoates [¹¹C]4a鈥?b>d were synthesized using Pd(0)-mediated rapid cross-coupling reactions employing [¹¹C]carbon monoxide and arylboronic acid neopentyl glycol esters 3a鈥?b>d under atmospheric pressure in methanol鈥揹imethylformamide (MeOH鈥揇MF), in radiochemical yields of 12 卤 5鈥?6 卤 13% (decay-corrected based on [¹¹C]O). The reaction conditions were highly favorable for the synthesis of [¹¹C]Am80 ([¹¹C]2) and [¹¹C]methyl 4-((5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)carbamoyl)benzoate ([¹¹C]2-Me) using 4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-N-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)benzamide (5), both of which produced a decay-corrected radiochemical yield (RCY) of 26 卤 13%, with >99% radiochemical purity and an average specific radioactivity of 44 GBq/渭mol. The yields of [¹¹C]4a, [¹¹C]2-Me, and [¹¹C]2 were improved by the use of a 2-fold excess of the solvents and reagents under the same conditions to give respective yields of 66 卤 8, 65 卤 7, and 48 卤 2%.

Keywords:

Am80; tamibarotene; methoxycarbonylation; [¹¹C]carbon monoxide