Abstract: This study focused on the first-line anticancer drug Alectinib, designing and synthesizing a furan-based intermediate through a three-step reaction sequence using cost-effective and readily available starting materials. The optimized protocol minimized intermediate isolation and purification steps, achieving completion within 8 hours with a consistent yield of 75%–80%, making it suitable for undergraduate laboratory instruction. Structural characterization by proton nuclear magnetic resonance spectrum (¹H NMR) and mass spectrometry (MS) enhanced students’ analytical skills while familiarizing them with standard organic synthesis workflows. The experiment successfully integrated ideological education (highlighting the national security significance of original drug development) with multidisciplinary knowledge spanning organic chemistry (condensation and substitution reactions), medicinal chemistry (bioisosterism), and spectroscopic analysis (NMR and MS). Designed to cultivate problem-solving abilities, this pedagogical approach introduces cutting-edge pharmaceutical research while fostering interdisciplinary thinking and lifelong learning principles. Through tiered learning objectives, the experiment accommodates diverse student capabilities, serving as an innovative model for integrating theoretical and practical education in organic and medicinal chemistry.

Key words: Principle of bioisosterism, Alectinib, Nucleophilic aromatic substitution, Condensation reaction, Proton nuclear magnetic resonance spectrum