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. Author manuscript; available in PMC: 2016 Mar 2.
Published in final edited form as: ACS Chem Neurosci. 2015 Dec 7;7(2):240–258. doi: 10.1021/acschemneuro.5b00286

Scheme 4. Synthesis of Fluoro-Substituted Benzimidazole Analoguesa.

Scheme 4

aReagents and conditions: (a) (i) H2, Pd/C, MeOH, rt; (ii) methyl 4-formylbenzoate, NaBH(OAc)3, AcOH, MeOH, rt; (iii) p-TsOH, toluene, 110 °C, for the synthesis of 29a; (b) (i) 10, K2CO3, DMF, 80 °C; (ii) Fe, AcOH, EtOH, 80 °C, for the synthesis of 29b; (c) NaOH, 50 wt % aq. NH2OH, THF/MeOH (1:1), 0 °C to rt.