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. Author manuscript; available in PMC: 2018 Nov 22.
Published in final edited form as: J Med Chem. 2017 Nov 9;60(22):9184–9204. doi: 10.1021/acs.jmedchem.7b00941

Scheme 7. Synthesis of analogs 51–57 a.

Scheme 7

aReagents and conditions: (a) MeCN, LDA, −78 °C, 4 h, 78–97% (b) Hantzsch ester, L-Pro, EtOH, 60 °C, 0.5 h, 86–98% (c) III, TsOH, EtOH, 150 °C, MW, 15 min, 60–77 % (d) TsOH, NaNO2, KI, MeCN, 12 h, 36–47% (e) 52: CuCN, DMSO, 160 °C, 0.5 h, 78% (f) 51, 53–55: requisite boronic acid, SiliCat-DPP-Pd, Na2CO3, DME, MW, 130 °C, 0.5h (g) 57: (1,10-Phenanthroline)(trifluoromethyl)copper(I), DMF, 55 °C, 1 h, 97% (i) LiOH, THF-MeOH, 1 h.