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. Author manuscript; available in PMC: 2017 Dec 5.
Published in final edited form as: Bioorg Med Chem Lett. 2014 Aug 15;24(19):4708–4713. doi: 10.1016/j.bmcl.2014.08.021

Scheme 3.

Scheme 3

Reagents and conditions: (a) ethyl 2-isocyanoacetate (1.2 equiv), CuI (0.2 equiv), Cs2CO3 (2 equiv,), DMSO, 80 °C, 16 h, 76%; (b) THF, NBS (1.0 equiv), rt, 2 h, 99%; (c) 6-methoxypyridin-3-yl phenylboronic acid (1.5 equiv), Pd(PPh3)4 (0.1 equiv), Na2CO3 (2.0 equiv), DMF–H2O (4:1), μw, 120 °C, 15 min, 65%; (d) K2CO3 (2 equiv), benzyl bromide (2 equiv, iodomethane applied for 17a), DMF, 45 °C, 16 h, 60–90%; (e) LiBH4, THF, rt, 16 h, 50–80%.