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Published in final edited form as: J Med Chem. 2021 Jan 26;64(3):1733–1761. doi: 10.1021/acs.jmedchem.0c02201

Scheme 3 — Reagents and conditions: (a) concentrated HCl, NaNO₂, H₂O, 0 °C, 15 min; (b) NaN₃, H₂O, room temperature, 2 h; (c) MeONa, 1-((4-(tert-butyl)phenyl)sulfonyl)propan-2-one, MeOH, 60 °C, overnight; (d) n-BuLi, THF, −78 °C, 5 min; (e) NFSI, THF, −78 °C, 1 h; (f) C₂Cl₆, THF, −78 °C, 1 h; (g) MeB(OH)₂, Pd(PPh₃)₄, Na₂CO₃, dioxane, H₂O, 120 °C, 5 h; (h) ethenylSn(Bu)₃, Pd(PPh₃)₄, toluene, 120 °C, 5 h; (i) H₂, 10% Pd/C, MeOH, THF, room temperature, 3 h; j) 4,4,5,5-tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolane, Pd(PPh₃)₄, Na₂CO₃, dioxane, H₂O, 120 °C, 5 h; (k) H₂, 10% Pd/C, MeOH, THF, room temperature, 3 h; (l) MeONa, CuCl₂, DMF, 130 °C, overnight; m) CO (1.5 MPa), Pd(dppf)Cl₂, MeOH, 80 °C, 24 h; (n) Zn(CN)₂, Pd(dppf)Cl₂, DMF, microwave, 160 °C, 15 min; (o) MeMgBr, THF, reflux, 15 h.

Scheme 3 — Reagents and conditions: (a) concentrated HCl, NaNO₂, H₂O, 0 °C, 15 min; (b) NaN₃, H₂O, room temperature, 2 h; (c) MeONa, 1-((4-(tert-butyl)phenyl)sulfonyl)propan-2-one, MeOH, 60 °C, overnight; (d) n-BuLi, THF, −78 °C, 5 min; (e) NFSI, THF, −78 °C, 1 h; (f) C₂Cl₆, THF, −78 °C, 1 h; (g) MeB(OH)₂, Pd(PPh₃)₄, Na₂CO₃, dioxane, H₂O, 120 °C, 5 h; (h) ethenylSn(Bu)₃, Pd(PPh₃)₄, toluene, 120 °C, 5 h; (i) H₂, 10% Pd/C, MeOH, THF, room temperature, 3 h; j) 4,4,5,5-tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolane, Pd(PPh₃)₄, Na₂CO₃, dioxane, H₂O, 120 °C, 5 h; (k) H₂, 10% Pd/C, MeOH, THF, room temperature, 3 h; (l) MeONa, CuCl₂, DMF, 130 °C, overnight; m) CO (1.5 MPa), Pd(dppf)Cl₂, MeOH, 80 °C, 24 h; (n) Zn(CN)₂, Pd(dppf)Cl₂, DMF, microwave, 160 °C, 15 min; (o) MeMgBr, THF, reflux, 15 h.