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. Author manuscript; available in PMC: 2019 Sep 19.
Published in final edited form as: ChemMedChem. 2018 Aug 19;13(18):1978–1987. doi: 10.1002/cmdc.201800411

Scheme 1.

Scheme 1.

Syntheses of sulfur-containing compounds. Reagents and conditions: (a) sodium methanesulfinate, DMSO, 100 °C; (b) sodium thiomethoxide, K2CO3, DMF, 55 °C; (c) H2O2, acetic acid, 55 °C; (d) (i) K2S2O5, TBAB, sodium formate, Pd(OAc)2, PPh3, 1,10-phenanthroline, DMSO, rt; (ii) NCS, methylamine or 2-fluoroethylamine, DIPEA, THF, rt; (e) (i) K2S2O5, TBAB, sodium formate, Pd(OAc)2, PPh3, 1,10-phenanthroline, DMSO, rt; (ii)1-bromo-3-fluoropropane, THF, rt; (f) 1,2-ethanedithiol, copper(II) sulfate pentahydrate, Cs2CO3, DMSO, rt; (g) 1-bromo-2-fluoroethane or 1-bromo-3-fluoropropane, TBAB, Cs2CO3, DMF, rt.