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. Author manuscript; available in PMC: 2017 Jan 14.
Published in final edited form as: J Med Chem. 2015 Dec 30;59(1):219–237. doi: 10.1021/acs.jmedchem.5b01276

Scheme 2.

Scheme 2

Synthesis of 2-(4-fluorophenyl)-benzothiophenesa

aReagents and conditions: (a) N-bromoacetamide, DCM/EtOH, rt, 2 h, 78%; (b) H2O2, TFA, DCM, 0 °C, 2 h, 75%; (c) 4-methoxyphenol, NaH, DMF, rt, 3 h, 93%; (d) LiAlH4, THF, 0 °C, 2 h, 71%; (e) BBr3, DCM, −78 °C to rt, overnight; (f) AlCl3, R1COCl, DCM, rt, 2-48 h.