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. Author manuscript; available in PMC: 2013 Jun 15.
Published in final edited form as: Bioorg Med Chem. 2012 May 4;20(12):3698–3702. doi: 10.1016/j.bmc.2012.04.056

Scheme 1.

Scheme 1

Synthesis of 5-(5-(6-methyl-3,6-diazabicyclo[3.2.0]heptan-3-yl)pyridin-2-yl)-1H-indole and its desmethyl precursor. Reagents and conditions: (a) Pd2(dba)3, BINAP, t-BuONa in toluene, at 85 °C 20 h, 83%; (b) Pd(PPh3)4, dioxane/Na2CO3 aq. 2M)=4:1, at 115 °C 1.5 h, 77%; (c) CF3CO2H-CH2Cl2, 27%; (d) HCHO, NaBH(OAc)3, CH3CN, 31%.