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. 2018 Mar 18;9(6):540–545. doi: 10.1021/acsmedchemlett.8b00011

Scheme 2. Preparation of Compounds 1820.

Scheme 2

Reagents and conditions: (a) ethylene glycol, toluene, TsOH, 100 °C, 98%; (b) DPPA, DEAD, PPh3, THF, 87%; (c) trimethylphosphine, THF/H2O, 85%; (d) formaldehyde, EtOAc, MeOH, 92%; (e) TsOH, acetone, 98%; (f) KHMDS, PhN(SO2CF3)2, THF, 95%; (g) Pd(PPh3)2Cl2, 7-isoquinoline boronic acid, Na2CO3, dioxane/H2O, 76%; (h) KOOCN=NCOOK, AcOH, DMSO, THF, 70%.