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Communication | Regular issue | Vol 22, No. 6, 1984, pp.1347-1350
Published online, 1st January, 1970
DOI: 10.3987/R-1984-06-1347
Synthesis of Indole and Related Compounds from Halo-nitroaromatics

Takao Sakamoto, Yoshinori Kondo, and Hiroshi Yamanaka*

*Pharmaceutical Institute, Pharmaceutical Institute, Aobayama, Sendai 980-8578, Japan

Abstract

5,7-Dimethyl-6-azaindole was synthesized by treatment of 3-amino-2,6-dimethyl-4-pyridineacetaldehyde diethyl acetal with hydrochloric acid in boiling ethanol. According to the similar manner, indole and ethyl 4-indolecarboxylate were obtained from the corresponding 2-aminophenylacetaldehyde derivatives in satisfactory yields. The starting materials were easily prepared by palladium-catalyzed cross-coupling reaction of o-halonitroaromatics with trimethylsilylacetylene followed by the reaction with sodium ethoxide and catalytic reduction of the o-nitro group.