Predicting reaction yield will help chemists optimize synthetic routes and methodology directly. In this approach, we developed prediction models on the two major types of Pd-catalyzed coupling reactions, including the Buchwald-Hartwig coupling reaction and Suzuki-Miyaura coupling reaction, which are broadly used in pharmaceutical synthesis. For Buchwald-Hartwig reaction, we used the high-throughput experimentation dataset from Doyle et al. In most circumstances, the catalytic cycle of the Buchwald-Hartwig reaction starts from oxidative addition of the aryl halide on the palladium, forming a Pd (II) intermediate. With isoxazole existing in the system, the N-O bond of it could undergo an oxidative addition, hence the palladium is chelated by the additive, impeding the catalytic cycle. According to the reaction mechanism of Buchwald-Hartwig reaction, we first chose 39 descriptors for the ligands, additives, bases, and aryl halides of each reaction (highlighted atoms and bonds in Figure ), which accurately describe the reactivity. Similar to the above enantioselectivity prediction process, we further analyzed the descriptors on the 10-times 70:30 random split and the important descriptors (five top-ranking) are listed in Figure . It is evident that 3 out of 5 critical descriptors are related to the electronic properties of isoxazole, validating the corresponding mechanism. For other types of reaction with unclear mechanism, in case Reaxtica could give gratifying outcomes, descriptor analysis may provide insights about the reaction.