Conjugate addition reactions of imidazo[1,2-a]pyridines with para-quinone methides were investigated for the first time under metal-free and additive-free conditions. Conjugate addition adducts of imidazo[1,2-a]pyridines were obtained in excellent yields. In addition, late-stage drug functionalization of a commercial drug Zolimidine was performed using para-quinone methides. All C3-alkylated imidazo[1,2-a]pyridines were obtained in good to excellent yields. More information can be found in the https://onlinelibrary.wiley.com/doi/10.1002/ajoc.202100313.