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. Author manuscript; available in PMC: 2014 Dec 12.
Published in final edited form as: J Med Chem. 2013 Dec 2;56(23):9709–9724. doi: 10.1021/jm4014136

Scheme 6.

Scheme 6

Synthesis of N-substituted analogues of 1a

aReagents and conditions: (a) 2-(1,3-dioxoisoindolin-2-yl)acetaldehyde, Na(OAc)3BH, DCE, CH3COOH, RT, 12 h (b) hydrazine, EtOH, reflux, 3 h; (c) 1,4-Cyclohexanedione monoethyleneketal, Na(OAc)3BH, CH3COOH, dichloroethane, RT, 12h ; (d) 3N HCl, diethylether, RT, 2 h; (e) indole, pyrrolidine, EtOH, reflux, 24 h.