Synthesis of 11C-amides using [11C]carbon monoxide and in situ activated amines by palladium-mediated carboxaminations

被引:41
作者
Karimi, F
Långström, B
机构
[1] Univ Uppsala, Inst Chem, Dept Organ Chem, S-75121 Uppsala, Sweden
[2] Uppsala Res Imaging Solut AB, S-75185 Uppsala, Sweden
关键词
D O I
10.1039/b209553j
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[C-11]Carbon monoxide at low concentrations, aryl halides and amines were used in the palladium-mediated synthesis of twenty C-11-amides. In the study several approaches to improve the radiochemical yield were explored. Eight of the selected amides were prepared by in situ activation of the amines using lithium bis(trimethylsilyl)amide and the radiochemical yields of these reactions were improved compared to utilising a previous reported method. In the synthesis of 1-[carbonyl-C-11]benzoyl-3-methyl-1H-indole (11) from 3-methyl-1H-indole (25), the corresponding organotin-amine was prepared prior to the acylation reaction. In a typical experiment, N-(4-hydroxyphenyl)-[carbonyl-C-11-]acetamide (5) was prepared in 15% radiochemical yield using 4-amninophenol (20) but the yield increased to 63% when the amine was activated by lithium bis(trimethylsilyl)amide.
引用
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页码:541 / 546
页数:6
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