Exploration of the annulation began with an initial survey of reaction conditions using 2-iodoaniline (1a) and propynyl BMIDA (2a) as a benchmark system (Table ). Optimization provided a system that delivered 2-BMIDA-3methylindole 3 in good yield (entry 1; for full details, see Supporting Information (SI)). These conditions were equivalent to more standard Larock-type conditions (entry 2); however, the chloride effect 7-9 could be replicated by the catalytic chloride available from the Pd catalyst, which delivered a small practical advantage. In the absence of chloride, reaction efficiency was ca. 20% lower (entry 3). The main issue that required to be navigated was compatibility of the reaction conditions with the BMIDA unit. For example, stronger bases led to MIDA hydrolysis and subsequent protodeboronation lowering the yield of 3 (entry 4).