Skip to main content
. Author manuscript; available in PMC: 2021 Jun 7.
Published in final edited form as: J Med Chem. 2011 Dec 22;55(1):515–527. doi: 10.1021/jm2014277

Scheme 3a.

Scheme 3a

aReagents and conditions: (a) ethyl 2-bromoacetate, NaOEt, EtOH, reflux, overnight; (b) NaOH, H2O, 80 °C, overnight; (c) oxalyl chloride, DCM, DMF, room temperature, 4 h; (d) N,O-dimethylhydroxylamine hydrochloride, DIEA, DCM, room temperature, 1 h; (e) N,O-dimethylhydroxylamine hydrochloride, K2CO3, Et2O, H2O, room temperature, 30 min; (f) phenylboronic acid, PdCl2(PPh3)2, K2CO3, dioxane, H2O, 100 °C, 16 h; (g) NaOEt, EtOH, 70 °C, overnight; (h) EtOAc, LiHMDS, THF, −78 °C, overnight; (i) NH2NH2, EtOH, room temperature, overnight.