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Synthesis 2011(19): 3089-3098  
DOI: 10.1055/s-0030-1260199
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

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

Hans-Peter Buchstaller*a, Kai Wilkinsona, Kasimir Burekb, Yasmin Nisarb
a Merck Serono, Merck KGaA, Frankfurter Straße 250, 64293 Darmstadt, Germany
Fax: +49(6151)723129; e-Mail: hans.peter.buchstaller@merck.de;
b Performance Materials, Merck KGaA, Frankfurter Str. 250, 64293 Darmstadt, Germany
Further Information

Publication History

Received 10 May 2011
Publication Date:
01 September 2011 (online)

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Abstract

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.

Key words

carbonylation - esters - amides - alkoxycarbonylation - aminocarbonylation - iodoindazole - palladium catalysis

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