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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 5.

Scheme 5.

Synthesis of sulfone analogs 7p, 7q, 7t, 7u and 7x (A – C), and spirocyclobutane anlogs 6p, 7h, 7i (D). Reagents and Conditions: a) MeSO2Na, CuI, L-Proline, NaOH, DMSO, 80 °C; b) ArSO2Cl, pyridine, DCM, r.t.; c) 2M LiOH, THF, 65 °C; d) DPPA, t-BuOH, DME, 100 °C; e) TFA, DCM, r.t.; f) Boc2O, MeOH, r.t.; g) NBS, AIBN, CCl4, 80 °C; h) TMSCN, K2CO3, MeCN, 0–50 °C; i) 1,3-dibromopropane, NaH, DMSO, r.t.; j) HCl, dioxane, 50 °C; k) 1,3-diiodopropane, KOtBu, THF, r.t.; l) tert-butylcarbamate, Pd2(dba)3, Xantphos, Cs2CO3, Toluene, 90 °C; m) H2NMe, THF, 65 °C.