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. Author manuscript; available in PMC: 2011 Aug 26.
Published in final edited form as: J Med Chem. 2010 Aug 26;53(16):6112–6121. doi: 10.1021/jm1005034

Scheme 1.

Scheme 1

Synthesis of (±)4- and 5-substituted citalopram analoguesa

a Reagents and conditions: (a) MeOH, conc. H2SO4, reflux, 12 h; (b) chromyl chloride, CCl4, 0°C ∼ reflux, 20 h; (c) THF, 0°C ∼ rt, 3 h; (d) THF, 0°C ∼ rt, overnight; (e) HCl/EtOH (1:1), 10 min; (f) Boronic acids, Na2CO3, Pd(PPh3)4, DME, H2O, 70–80°C, overnight; (g) CuI, KI, HMPA, 150°C, 3h.