Introduction of substituents in the pyridine proton of 7-azaindoline

Electropilic substitution (nitration, bromination, and chlorination) of 4-methyl-6-chloro-7-azaindoline (and its N-acetyl derivative) takes place in the 5 position. 4-Methyl-5-amino-7-azaindoline, 4-methyl-5-nitro-7-azaindoline, and 1-acetyl-4-methyl-5-amino-6-chloro-7-azaindoline were obtained by reduction of 1-acetyl-4-methyl-5-nitro-6-chloro-7-azaindoline under various conditions. A method was developed for the preparation of a new three-ring system — 1,2,3-oxadiazolo5,4-b]-pyrrolo2,3-e]pyridine.Communication L from the series Derivatives of Azaindoles. See 1] for communication XLIX.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 380–384, March, 1977.