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Synthesis of B10. Reagents and conditions: (A) (1) 8-methoxy-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline, Pd(dppf)Cl2, K2CO3, dioxane/H2O, reflux, 2.5 h; (2) KOH, MeOH, 60 °C, 1.5 h; (3) 40% HBr, reflux, 24 h; (B) TBSCl, imidazole, DMF, 0.5 h; (C) (1) N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)pyridin-4-amine, Pd(PPh3)4, Na2CO3, toluene, EtOH, H2O, 100 °C, 6 h; (2) TBAF, THF, 0.5 h.
