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. 2015 Oct 6;6(11):1128–1133. doi: 10.1021/acsmedchemlett.5b00215

Scheme 1. Synthesis of Pyridines 10–17.

Scheme 1

Conditions: (a) 4-ClPhB(OH)2 (21) or (4-SO2Me)PhB(OH)2 (22), Pd(dppf)Cl2, Na2CO3, dioxane, H2O, 110 °C or KOH, PhCH3, EtOH, H2O, 140 °C; (b) (4-CONH2) PhB(OH)2 (23) or PhB(OH)2 (24), (4-OH)PhB(OH)2 (25), or (pyridin-2-NH2)-B2Pin2, (26), or (pyrimidin-2-NH2)Bpin (27); catalyst: Ph(AmPhos)2Cl2, Pd(dppf)Cl2, or Pd(Ph3P)4; base: Na2CO3, K2CO3, Cs2CO3, or KOH; solvent: EtOH, THF, PhCH3, or dioxane, H2O, heat; (c) B2Pin2 (26), Pd(dppf)Cl2, KOAc, dioxane, 60 °C; (d) 5-bromopyridin-2-ol (28) or 4-chloropyridin-2-ol (29), Pd(dppf)Cl2, Na2CO3, dioxane, H2O, 110 °C.