For a medicinal chemistry project, we sought diverse amidomethylated derivatives (1─8) of 4-chloro-3-fluoropyridine (9). Our synthesis objectives emphasized regioselectivity for derivatization at the 2-position, scalability for large-scale production (up to hundreds of grams), and efficiency with a minimal number of synthetic steps. This strategic approach aimed to provide a versatile array of compounds, ensuring suitability for various applications within the project's scope. By focusing on these key criteria, we aimed to streamline the synthetic process, making it robust, scalable, and conducive to meeting the demands of the medicinal chemistry endeavor.