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. 2018 Sep 14;9(10):1007–1012. doi: 10.1021/acsmedchemlett.8b00269

Scheme 1. Synthesis of 4-Aryl Quinolines.

Scheme 1

Reagents: (i) iPrMgCl·LiCl, CuBr·SMe2, THF, 0 °C, 47%; (ii) NaBH4, THF/EtOH (5:1), 0 °C, 30 min, 77%; (iii) 4 N HCl, THF, rt, 1 h then NaI, MeCN, 90 °C, 16 h, 99%; (iv) HClO4, t-BuOAc, rt, 3 h, 74%; (v) Pd[PPh3]4, K2CO3, Ar–B(OH)2, DMF, 90 °C, 3 h, 38–97%; (vi) 2 N NaOH, EtOH, 60 °C, 3 h, 11–96%.