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. Author manuscript; available in PMC: 2020 Jan 24.
Published in final edited form as: J Med Chem. 2019 Aug 9;62(16):7489–7505. doi: 10.1021/acs.jmedchem.9b00625

Scheme 3.

Scheme 3.

Synthesis of Compounds 14a–d

Reagents and conditions: (a) NaH, DMF; (b) NaNO2, trifluoroacetic acid; (c) POCl3, DMF (cat), 95 °C; (d) 9h, MeCN, 1,4-dioxane, 80 °C; (e) mCPBA or Davies oxazirdine, DCM; (f) NH3, MeOH, THF, 65 °C; (g) Trifluoroacetic acid, DCM; (h) R(BOH)2, Pd(dppf)Cl2, Na2CO3, dioxane, water, 80 °C.