Synthesis of 3-Indazolecarboxylic Esters and Amides via Pd-Catalyzed Carbonylation of 3-Iodoindazoles

被引:9
作者
Buchstaller, Hans-Peter [1 ]
Wilkinson, Kai [1 ]
Burek, Kasimir [2 ]
Nisar, Yasmin [2 ]
机构
[1] Merck KGaA, Merck Serono, D-64293 Darmstadt, Germany
[2] Merck KGaA, Performance Mat, D-64293 Darmstadt, Germany
来源
SYNTHESIS-STUTTGART | 2011年 / 19期
关键词
carbonylation; esters; amides; alkoxycarbonylation; aminocarbonylation; iodoindazole; palladium catalysis; PRACTICAL SYNTHESIS; DERIVATIVES; INDAZOLES; ANTAGONISTS; RECEPTOR;
D O I
10.1055/s-0030-1260199
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A straightforward and effective procedure for the preparation of 1H-indazole-3-carboxylic acid esters and amides was developed. A series of functionalized 3-iodoindazoles were subjected to Pd-catalyzed carbonylations in the presence of methanol or amines, yielding the title compounds in moderate to good yield. For the majority of examples, the reaction proceeded cleanly under mild conditions, which were readily tolerated by a diverse range of functional groups that allow further synthetic transformations.
引用
收藏
页码:3089 / 3098
页数:10
相关论文
共 28 条
[1]  
Aletru M., 2009, PCT Int. Appl., Patent No. 2009010660
[2]  
ALISI MA, 2009, Patent No. 2009062883
[3]  
ARRINGTON KL, 2006, Patent No. 2006086255
[4]   Palladium-Catalyzed Carbonylation-A Reaction Come of Age [J].
Barnard, Christopher F. J. .
ORGANOMETALLICS, 2008, 27 (21) :5402-5422
[5]   PHASE-TRANSFER CATALYZED SYNTHESIS OF INDAZOLES FROM ORTHO-ALKYLBENZENEDIAZONIUM TETRAFLUOROBORATES [J].
BARTSCH, RA ;
YANG, IW .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1984, 21 (04) :1063-1064
[6]   Disubstituted indazoles as potent antagonists of the integrin αvβ3 [J].
Batt, DG ;
Petraitis, JJ ;
Houghton, GC ;
Modi, DP ;
Cain, GA ;
Corjay, MH ;
Mousa, SA ;
Bouchard, PJ ;
Forsythe, MS ;
Harlow, PP ;
Barbera, FA ;
Spitz, SM ;
Wexler, RR ;
Jadhav, PK .
JOURNAL OF MEDICINAL CHEMISTRY, 2000, 43 (01) :41-58
[7]   Palladium-Catalyzed Carbonylation Reactions of Aryl Halides and Related Compounds [J].
Brennfuehrer, Anne ;
Neumann, Helfried ;
Beller, Matthias .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (23) :4114-4133
[8]   THE SEROTONIN 5-HT4 RECEPTOR .2. STRUCTURE-ACTIVITY STUDIES OF THE INDOLE CARBAZIMIDAMIDE CLASS OF AGONISTS [J].
BUCHHEIT, KH ;
GAMSE, R ;
GIGER, R ;
HOYER, D ;
KLEIN, F ;
KLOPPNER, E ;
PFANNKUCHE, HJ ;
MATTES, H .
JOURNAL OF MEDICINAL CHEMISTRY, 1995, 38 (13) :2331-2338
[9]  
Buchler I. P., 2009, Patent No. [WO2009106980A2, 2009106980]
[10]  
Buchler I. P., 2009, Patent No. [WO2009106982A1, 2009106982]