The synthesis of 5‐azaindoles by substitution‐rearrangement of 7‐azaindoles upon treatment with certain primary amines

Certain 4‐substituted 1 H ‐pyrrolo[2,3‐ b ]pyridines (7‐azaindoles) undergo a nucleophilic substitution‐rearrangement upon treatment with various primary amines at elevated temperatures to yield N ‐1‐substituted 4‐amino‐1 H ‐pyrrolo[3,2‐ c ]pyridines (5‐azaindoles). Treatment of the same 7‐azaindoles with secondary amines under the same reaction conditions led to simple nucleophilic substitution products.