Synthesis of 4-[18F]fluoroiodobenzene and its application in sonogashira cross-coupling reactions

被引：48

作者：

Wüst, FR ^{[1
]}

Kniess, T ^{[1
]}

机构：

[1] FZ Rossendorf eV, Inst Bioanorgan & Radiopharmazeut Chem, Dresden, Germany

来源：

JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS | 2003年 / 46卷 / 08期

关键词：

F-18]fluoroiodobenzene; sonogashira cross-coupling; F-18-labelled steroids;

D O I：

10.1002/jlcr.709

中图分类号：

Q5 [生物化学];

学科分类号：

071010 ; 081704 ;

摘要：

The first application of a Sonogashira cross-coupling reaction in F-18 chemistry has been developed. The reaction was exemplified by the cross-coupling of terminal alkynes (ethynylcyclopentyl carbinol 6, 17alpha ethynyl-3,17beta-estradiol 7 and 17alpha-ethynyl-3-methoxy-3,17beta-estradiol 8) with 4-[F-18]fluoroiodobenzene. 4,4'-Diiododiaryliodonium salts were used as precursors for the synthesis of 4-[F-18]fluoroiodobenzene, enabling the convenient access to 4-[F-18]fluoroiodobenzene in 13-70% yield using conventional heating or microwave activation. The Sonogashira cross-coupling of 4-[F-18]fluoroiodobenzene with terminal alkynes gave the corresponding 4-[F-18]fluorophenylethynyl-substituted compounds [F-18]-9, [F-18]-10 and [F-18]-13 in yields up to 88% within 20 min of starting from 4-[F-18]fluoroiodobenzene. Copyright (C) 2003 John Wiley Sons, Ltd.

引用

页码：699 / 713

页数：15

共 25 条

[1] Synthesis of 4-[18F]fluorophenylalkenes and -arenes via palladium-catalyzed coupling of 4-[18F]fluoroiodobenzene with vinyl and aryl tin reagents [J].

Allain-Barbier, L ;

Lasne, MC ;

Perrio-Huard, C ;

Moreau, B ;

Barre, L .

ACTA CHEMICA SCANDINAVICA, 1998, 52 (04) :480-489

[2] DIARYLIODONIUM SALTS .9. THE SYNTHESIS OF SUBSTITUTED DIPHENYLIODONIUM SALTS [J].

BERINGER, FM ;

FALK, RA ;

KARNIOL, M ;

LILLIEN, I ;

MASULLO, G ;

MAUSNER, M ;

SOMMER, E .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1959, 81 (02) :342-351

[3] PREPARATION OF NCA [17-F-18]-FLUOROHEPTADECANOIC ACID IN HIGH YIELDS VIA AMINOPOLYETHER SUPPORTED, NUCLEOPHILIC FLUORINATION [J].

COENEN, HH ;

KLATTE, B ;

KNOCHEL, A ;

SCHULLER, M ;

STOCKLIN, G .

JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 1986, 23 (05) :455-466

[4] Synthesis of [4-18F]-1-bromo-4-fluorobenzene and its use in palladium-promoted cross-coupling reactions with organostannanes [J].

Forngren, T ;

Andersson, Y ;

Lamm, B ;

Langstrom, B .

ACTA CHEMICA SCANDINAVICA, 1998, 52 (04) :475-479

[5]

Gail R., 1997, Journal of Labelled Compounds and Radiopharmaceuticals, V40, P50

[6] Improved methods for the synthesis of [ω-11C]palmitic acid [J].

Hostetler, ED ;

Fallis, S ;

McCarthy, TJ ;

Welch, MJ ;

Katzenellenbogen, JA .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (04) :1348-1351

[7] Important fluorinated drugs in experimental and clinical use [J].

Ismail, FMD .

JOURNAL OF FLUORINE CHEMISTRY, 2002, 118 (1-2) :27-33

[8] Synthesis of 3-[(2S)-azetidin-2-ylmethoxyl-5-[11C]-methylpyridine, an analogue of A-85380, via a stille coupling [J].

Karimi, F ;

Långström, B .

JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 2002, 45 (05) :423-434

[9] Biologically active 11C-labeled amides using palladium-mediated reactions with aryl halides and [11C]carbon monoxide [J].

Kihlberg, T ;

Långström, B .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (25) :9201-9205

[10] Compounds labelled with short-lived β+-emitting radionuclides and some applications in life sciences.: The importance of time as a parameter [J].

Långström, B ;

Kihlberg, T ;

Bergström, M ;

Antoni, G ;

Björkman, M ;

Forngren, BH ;

Forngren, T ;

Hartvig, P ;

Markides, K ;

Yngve, U ;

Ögren, M .

ACTA CHEMICA SCANDINAVICA, 1999, 53 (09) :651-669

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