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. 2020 Apr 7;11(5):713–719. doi: 10.1021/acsmedchemlett.9b00561

Scheme 2. Synthesis of Compound 8.

Scheme 2

Reagents and conditions: (a) MeOH, H2SO4, reflux, 12 h; (b) KOAc, Pd(dppf)Cl2, bis(pinacolate)diboron, DCM, dioxane, 80 °C, overnight; (c) H2, Pd/C 10%, EtOAc, RT, 12 h; (d) MeOH, H2SO4, reflux, 12 h; (e) NaOAc, Pd(dppf)Cl2 DCM, dioxane, 125 °C, 12 h; (f) neat POCl3, reflux, 2 h.