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. 2018 Jul 13;9(8):821–826. doi: 10.1021/acsmedchemlett.8b00215

Scheme 1. Synthesis of Compounds 16–20 as a Representative Route to 5-Aryl Oxindoles/Benzimidazolones.

Scheme 1

Reagents and conditions: (a) nBuLi, THF, −78 °C, then I2, 85%; (b) MOMCl, KOtBu, THF, 0 °C to rt, 65%; (c) nBuLi, THF, −78 °C, then I2, 47%; (d) 4 N HCl, dioxane, 93%; (e) Na(CO2CF2Cl), Cs2CO3, DMF/H2O, 100 °C, 27%; (f) CBr2F2, NaH, KOtBu, DMF, 80 °C, 15%; (g) AgBF4, DCM, −78 °C to rt, 62%; (h) NBS, MeCN, 0 °C, 72%; (i) B2(Pin)2, KOAc, cat Pd(dppf)Cl2–CH2Cl2, dioxane, 85 °C, 54–75%; (j) K3PO4, cat Pd(dppf)Cl2CH2Cl2 or Pd(dtbpf)Cl2, dioxane/H2O, 95 °C, 37–62%.