The formation of an amide bond is one of the most important reactions in the pharmaceutical industry. TBD has been shown to be an effective catalyst in facilitating the amidation of esters by primary and secondary amines (Fig- ), including demonstration on >10 kg scale. Despite its tremendous potential in improving sustainability, TBD-catalyzed amidation has received surprisingly little attention. Accordingly, this provides a perfect opportunity to incorporate a data-rich workflow for reaction optimization and understanding of substrate effects. Continuous flow processing can act as an enabling technology to apply high pressure and temperature and intensify the reaction. In our investigation, combinations of 5 esters (1a-e) and 3 amines (2a-c) have been examined with this dual modeling approach.