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. 2019 Feb 14;62(7):3254–3267. doi: 10.1021/acs.jmedchem.8b01719

Scheme 2. Representative Synthesis of Heteroaromatic Analog (Compound 31).

Scheme 2

Conditions: (i) AcOH, 100 °C, 67%; (ii) NaOH, THF, MeOH, H2O, 100 °C, 100%; (iii) MeNH2·HCl, HATU, DIEA, DMF, 95%; (iv) (BPin)2, PdCl2(dppf)·CH2Cl2, KOAc, dioxane, 80 °C; and (v) NaIO4, NH4OAc, H2O, THF, 24% over 2 steps.