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Paper | Regular issue | Vol 55, No. 12, 2001, pp.2289-2304
Published online, 1st January, 1970
DOI: 10.3987/COM-01-9320
Regioselective ortho-Directed Metalation and Electrophilic Substitution of Indole- and Indoline-5-(N-phenyl)carboxamides

Jean-François Rousseau and Robert H. Dodd*

*Institut de Chimie des Substances Naturelles, Centre National de la Recherche Scientifique, Avenue de la Terrasse, Bat. 27, 91198 Gif-sur-Yvette Cedex, France


Treatment of 1-(N,N-dimethylsulfamoyl)-1H-indole-5-(N-phenyl)carboxamide (1) with s-butyllithium at -80°C in THF followed by addition of an electrophile gave exclusively the product of C-2 substitution. A second metalation-substitution cycle on this product led to incorporation of the electrophile exclusively at C-4. In the case of the analogous indoline derivative (2), the first o-metalation occurred at C-4 while C-6 was the site of the second o-metalation.