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. Author manuscript; available in PMC: 2020 Jun 5.
Published in final edited form as: ChemMedChem. 2019 Apr 10;14(11):1096–1107. doi: 10.1002/cmdc.201900114

Scheme 3.

Scheme 3.

Synthesis of PRP 10. Reagents and conditions: a) Pd(OAc)2, NaOAc, NMP, 120 °C, 1 h; b) propargylamine, STAB-H, DCE, 16 h; c) perfluorobenzylbromide, K2CO3, CH3CN, 14 h; d) LiOH, 2:1 THF/H2O, 20 h; e) 19, EDC•HCl, HOBt, DMAP, Et3N, CHCl3, 6 h; f) NaN3, Bu4NN3, DMF,75–80 °C, 18 h; g) MgBr2, DCM, 3 h.