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. Author manuscript; available in PMC: 2020 Aug 30.
Published in final edited form as: ACS Infect Dis. 2020 Apr 20;6(5):922–929. doi: 10.1021/acsinfecdis.9b00524

Scheme 3.

Scheme 3

Reagents and conditions: (a) alkyl halide, NaH, DMF, 0 °C to rt, 15–51%; (b) Fe(s), EtOH, AcOH, H2O, rt, 2 h, 48–67% or Pt/C, H2, EtOAc, rt, 18 h, 70%; (c) 2-chloro-1,1,1-trimethoxy-ethane, p-TsOH·H2O, DCM, rt, 4 h, 26–87%; (d) 14 or 15, K2CO3, DMF, 50 °C, 18 h, 16–86%; (e) HF-pyridine, THF, rt, 3 h, 58%.