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. Author manuscript; available in PMC: 2014 Dec 19.
Published in final edited form as: Chem Biol. 2013 Dec 12;20(12):1536–1546. doi: 10.1016/j.chembiol.2013.11.005

Figure 2.

Figure 2

(a) Preparation and photolysis of BHQ-OPh. (a) MsCl, DIEA, THF, rt, 2 h, 68%; (b) phenol, 1 M KOH (aq.), THF, 72%; (c) TFA, MeOH. Time courses for the photolysis of BHQ-OPh are shown in Figure S1. (b) Preparation of BHQ-O-5HT. (a) MsCl, DIEA, THF, rt, 2 h, 68%; (b) K2CO3, CH3CN, reflux, 48 h, 78%; (c) TFA, CH2Cl2, rt, 1 h, 57%. (c) Preparation of BHQ-N-5HT. (a) carbonyldiimidazole, THF, rt, 2 h, 63%; (b) DMF, 60 ○C, 12 h, 65%; (c) TBAF, THF, rt 15 min, 85%; (d) conc. HCl (tr), MeOH, rt, 12 h, 55%.