The reaction class that we targeted for our experimental MTBO study was the palladium-catalyzed C-H activation reaction, reported by Hennessy and Buchwald, yielding pharmaceutically relevant oxindoles (16) from their corresponding chloroacetanilides (15), as shown in Scheme 2. Each case study is shown in Table and is highlighted if it is forming a potential bioactive fragment or active pharmaceutical ingredient (API) intermediate. The rationale behind these studies is two-fold: firstly, these oxindoles are closely related to many known bioactive molecules and hence medicinal chemistry projects, and secondly, when considering optimal growth vectors for bioactive molecular fragments to grow into more potent drug candidates (such as in FBDD), the most beneficial transformations are often exploiting C-H bonds on the fragment to form new C-C bonds. Therefore, using MTBO, we aimed to rapidly optimize several transformations using different starting materials with unique functionalities to yield structurally diverse oxindole products by forming valuable sp 2 -sp 3 C-C bonds. Then, for future optimization campaigns requiring oxindole syntheses, this model can be employed to expediate reaction optimization and process development for new substrates.