The northern fragment of TMC-95A has an oxidized indole sidechain, which can be synthesized from N-Boc-L-tryptophan. The 5-chloro group can be selectively removed from the 5,7-dichloro tryptophan derivative leaving the 7-chloro analog as the major product. Model studies were also done on 5,7-dibromo-3-methyloxindole and 5,7-dibromo-3-hydroxy-3-methyloxindole to confirm if selective reduction of the 5-bromo group is applicable to these oxindole ring systems.