A regioselective synthesis of N-carbomethoxy-2, 3, 5-tribromoindole (6) via a sequential one- pot bromination-aromatization-bromination of N-carbomethoxyindoline (2) is described. The process for the transformation of 2 into 6 permitted the isolation of stable reaction intermediates N-carbomethoxy-5-bromoindoline (3), N-carbomethoxy-5-bromoindole (4), and N-carbomethoxy-3, 5-dibromoindole (5). Compound 6 was used to complete the total ...