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. Author manuscript; available in PMC: 2015 Mar 15.
Published in final edited form as: Bioorg Med Chem Lett. 2014 Feb 7;24(6):1538–1544. doi: 10.1016/j.bmcl.2014.01.079

Scheme 2.

Scheme 2

Synthesis of benzophenone-functionalized tag-free probes 10a–b.a

aReagents and conditions. a) LDA, 1h; then ethyl 3,3-dimethyl acrylate, ZnI2, diglyme, −78°C – RT, 2h, 50%; b) (Bu3Sn)2, Pd(PPh3)4, toluene, reflux, 16h, 37%; c) 1 atm CO, PdCl2(PPh3)2, iodobenzene, DMF, 60°C, 4h, 58%; d) allyl isothiocyanate, AcOH, EtOH, 70°C, 16h, 27%; e) propargyl bromide or 12, Cs2CO3, 2-butanone, 70°C, 16h, 69–70%; f) Ts-Cl, pyridine, 0–4°C, 24h, 72%; g) nBuLi, −78°C, THF, 2h, then TBS-OTf, −78°C-RT, 1h, 63%.