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Synthesis of thienopyridone 1. Reagents and conditions: (i) Pd(PPh3)4, PhB(OH)2, Na2CO3, dioxane/H2O, µW 90 °C, 2 h, 95% (ii) Br2, CHCl3/AcOH, room temperature, 20 h, 98%; (iii) malonic acid, pyridine, piperidine, reflux, 5.5 h, 88%; (iv) SOCl2, DMF, toluene, reflux, 2.5 h; (v) NaN3, toluene/H2O, 0 °C to room temperature, 1.5 h, 44% (2 steps); (vi) Ph2O, µW 250 °C, 30 min, 52%; (vii) HNO3, H2SO4, 1 h, 80 °C; (viii) H-cube (1 atm), 10% Pd/C, 50 °C, 1 h, 9% (2 steps).
