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Synthesis of tepotinib-based c-MET degraders D1–D9. Reagents and conditions: (A) Synthesis of intermediate 6 and 8: (a) PPh3, DIAD, THF (dry), 0 °C, 12 h; (b) Pd(dppf)2Cl2, K3PO4, DMF/H2O, 80 °C, 10 h; (c) PPh3, CCl4, DCM, 45 °C, 12 h; (d) K2CO3, DMF, 80 °C, 10 h; (e) CF3COOH, DCM, 6 h; (f) K2CO3, DMF, 10 h; (g) CF3COOH, DCM, 6 h. (B–C): (a) THF, 55 °C, 12 h; (b) DIPEA, DMF, 24 h.
