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. Author manuscript; available in PMC: 2021 Aug 3.
Published in final edited form as: J Med Chem. 2019 Nov 20;63(5):2527–2546. doi: 10.1021/acs.jmedchem.9b01506

Scheme 1.

Scheme 1.

Synthesis of compounds 9a-s. Reagents and reaction conditions: a) SOCl2, 75 °C, 4 h (quant.). b) 2-aminophenol, TEA, DCM, 0 °C to rt, 12 h (87%). c) K2CO3, DMF, rt, 36 h (72%). d) Lawesson’s reagent, toluene, 100 °C, 12 h (68%). e) Hydrazine, dioxane, 85 °C, 3 h (89%). f) Acetic anhydride, 100 °C, 3 h (93%). g) B2(pin)2, KOAc, PdCl2(dppf)·CH2Cl2, dioxane, 145 °C, μw, 1 h (65%). h) Aryl halide, K2CO3, Pd(PPh3)4, 3:1 dioxane:water, 100 °C, 4 h (10–74%).