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. 2024 Nov 13;14(49):36352–36369. doi: 10.1039/d4ra07074g

Scheme 4. Synthesis of MQ237. Reagents, conditions and yields: (a) MsCl, Et3N, CH2Cl2, 0 °C, 2 h, (98%); (b) LiBr, DMF, 130 °C, 90 min, (91%); (c) NaBH4, EtOH, 23 °C, 1 h, (95%); (d) HCO2H, 30% H2O2, 23 °C, 2 h, (81%); (e) TBSCl, imidazole, DMF, 23 °C, 16 h, (86%); (f) C2(CN)4, 3-butyn-1-ol, 23 °C, 72 h, (44%); (g) ClCH2OMe, (i-Pr)2NEt, CH2Cl2, 23 °C, 16 h, (78%); (h) TBAF, THF, 23 °C, 16 h, (71%); (i) 3-[4-(Iodomethyl)phenyl]-3-(trifluoromethyl)-3H-diazirine, Bu4NI, NaH, THF, reflux 16 h, (52%); (j) 6 N HCl, THF, 23 °C, 2 h, (68%); (k) (1) SO3–Me3N, pyridine, 23 °C, 15 h; (2) 7 N NH3 in MeOH, (MQ237, 30%).

Scheme 4