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. Author manuscript; available in PMC: 2015 Apr 21.
Published in final edited form as: ACS Chem Biol. 2015 Jan 27;10(4):1054–1063. doi: 10.1021/cb5007536

Figure 3.

Figure 3

Synthesis of ZIMIR-HaloTag. (a) KOtBu, ethyl bromoacetate, THF, r.t., overnight, 60%; (b) TFA, DCM, r.t., overnight; (c) K2CO3, tert-butyl bromoacetate, CHCl3, r.t., overnight, 50% (steps b and c); (d) AlCl3, nitrobenzene, r.t., 16 h, 91%; (e) CH3SO3H, resorcinol, 90 °C, 24 h; (f1) Cs2CO3, Piv2O, DMF, 2 h, 48%; (f2) NBS, BPO, CCl4, 4 h, 84% (both isomers); (g) NaI, proton sponge, CH3CN, reflux, overnight, 70%; (h) NaSH, MeOH/THF/H2O (4:1:1), reflux, 1 h, 90%; (i) Na2SO4, NaCNBH3, MeOH, 34%; (j1) PyBOP, DMF, r.t., overnight, 50%; (j2) TFA, DCM, r.t., 4 h.