Collect. Czech. Chem. Commun.
2006, 71, 679-690
https://doi.org/10.1135/cccc20060679
A Study of 5-Nitroindole Alkylation
Václav Kozmíka, Bedřich Košataa, Jiří Svobodaa,* and Miroslav Kuchařb
a Department of Organic Chemistry, Institute of Chemical Technology, Prague, 166 28 Prague 6, Czech Republic
b Zentiva, 102 01 Prague 10, Czech Republic
Abstract
A detailed study of the 5-nitroindole alkylation, the key step in the synthesis of Zafirlukast, is presented. A broad distribution of alkyl derivatives has been found. 2,3- And 1,3-dialkylindoles can be selectively obtained in a ZnBr2-catalyzed reaction. Structure of all the products was fully assigned.
Keywords: Indoles; Alkylations; Lewis acid catalysis; Electrophilic substitutions; Friedel-Crafts alkylation; Leukotriene antagonists.
References: 33 live references.
