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. 2016 Jan 15;26(2):355–360. doi: 10.1016/j.bmcl.2015.12.003

Scheme 1.

Scheme 1

Reagents and conditions: (i) sealed tube, 1,4-dioxane, CuI (5.0 mol %), NaI, racemic trans-N,N′-dimethyl-1,2-cyclohexanediamine (10 mol %), 110 °C, N2, 18 h; (ii) 2-bromothiophene or 69, DMSO, KF, PdCl2(PPh3)2, AgNO3, 100 °C, N2, 2 h; (iii) toluene/EtOH, 2 M Na2CO3, PdCl2(dppf)·CH2Cl2, 85–90 °C, N2, 2–6 h; (iv) thiophene-2-boronic acid, toluene/EtOH, 2 M Na2CO3, PdCl2(dppf)·CH2Cl2, 85 °C, N2, 2 h.