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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 1.

Scheme 1.

Synthesis of sulfonamides, and the requisite aniline building blocks to compounds 5. Reagents and conditions: a) Pyridine, DCM, r.t.; b) HSO3Cl, 0 °C– r.t.; c) HNO3. H2SO4, DCM, 0 °C– r.t.; d) H2, Pd/C, MeOH, r.t.; e) ArSO2Cl, pyridine, DCM, r.t.; f) Benzyl bromide, K2CO3, MeCN, Δ; g) Cyclopropylboronic acid, Pd(OAc)2, PCy3.HBF4, K3PO4, Toluene, 80 °C; h) 3,3,3-trifluoroprop-1-ene, Pd(dppf)Cl2.DCM, K2CO3, dioxane, water, 70 °C; i) Ph2MeSBF4, LiHMDS, THF, −78 °C.