The ideation of scalable and reliable synthetic routes for the preparation of Active Pharmaceutical Ingredients (APIs) is an essential step in the workflow towards the approval of a new drug candidate. Ideally, this synthetic plan should guarantee sufficient robustness across different scales, from mg to decagram in the initial phases, leading to multi-kilogram processes to ensure expedite translation when the commercialization of bioactive compound is approaching. However, the reality behind the thinking process does not adhere with this principle, due to the conceptual differences between the drug discovery and the process development route requirements. In the discovery phase, the candidates are generally synthesized in the most modular and versatile way to enable the variation of key molecular fragments. When the first part of the campaign is complete, the route is usually not amenable to be performed on large scale, due to the toxic/hazardous reagents involved or to the prohibitive costs associated with the reactants. Hence, process chemists have to redesign the synthetic sequence in order to obtain scalable protocols.