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. Author manuscript; available in PMC: 2019 Dec 27.
Published in final edited form as: J Med Chem. 2019 Dec 5;62(24):11232–11259. doi: 10.1021/acs.jmedchem.9b01411

Scheme 3.

Scheme 3.

Synthesis of pentafluorosulfonyl products from commercial bromide intermediate, 30. Reagents and conditions: a) Phenyl formate, phenol, Pd(OAc)2, PtBu3.HBF4, Et3N, MeCN, 90 °C; b) BBr3, DCM, −78 °C; c) LiOH, THF, 65 °C; d) HNO3, H2SO4, DCM, 0 °C; e) H2SO4, MeOH, 65 °C; f) H2, Pd/C, MeOH, r.t.; g) ArSO2Cl, pyridine, DCM, r.t.; h) Amine, THF, 65 °C; i) Br2, FeCl3, AcOH, 0 °C; j) S2(CH3)2, Cu, pyridine, 115 °C, k) Oxone, EtOH, H2O, r.t.; k)