To explore the chemical as well as the emissive scope of the borindolizine scaffold, a series of substituted 2-methylpyridines were subjected to the standard reaction conditions (Scheme 1). Precursors for borindolizines 3a -3g were derived from 2-pyridylacetic acid through standard amide bond-forming conditions. Ester-substituted borindolizines 3a, 3b, 3d, 3e, and 3g were synthesized from their corresponding protected 2-pyridylacetates. Lower yields were observed for Weinreb amide 3e and tert-butyl ester 3g due to the limited stability of the lithiated carbanion. Pyridyl 1,3,4-oxadiazole precursor 1c heteroaryl-substituted borindolizine 3c in a 33% yield. Sulfone 1f was similarly deprotonated and borylated to form borindolizine 3f in a 54% yield. The emission wavelengths of the 2pyridylacetic acid-derived borindolizines were observed to be between 431 -458 nm (violet-blue), wherein the 1,3,4-oxadiazole substituted borindolizine 3c was observed to have the highest emission wavelength (458 nm).