Abstract Certain 4-substituted 1H-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-1H-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.