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. Author manuscript; available in PMC: 2014 Apr 1.
Published in final edited form as: Bioorg Med Chem Lett. 2013 Feb 13;23(7):2035–2043. doi: 10.1016/j.bmcl.2013.02.019

Scheme 3.

Scheme 3

Synthesis of thienyl phenyl ethers. Reagents and conditions: (b) BBr3, CH2Cl2, −78 °C to room temp, 6 h; (f) amine, HOBt, EDCI, DIEA, CH2Cl2, 0 °C to rt, overnight, 40–60%; (h) NaClO2, DMSO, NaH2PO4, THF/t-BuOH/H2O; (i) 5- bromothiophene-2-carbaldehyde, K2CO3, DMSO, 80 °C, overnight, 60%; (j) amine, NaBH(OAc)3, AcOH, CH2Cl2, 0 °C to room temperature, 1 h.