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. 2012 Feb 27;55(6):2894–2898. doi: 10.1021/jm201212h

Scheme 2. Synthetic Route to Compounds 11a–d.

Scheme 2

Reagents and conditions: (a) EtOH, Pd(OAc)2, Xantphos, DBU, Mo(CO)6, microwave 120 °C, 30 min, 93%; (b) 2-fluoro-4-methylpyridine, NaHMDS, THF, 0 °C, 2 h, 64%; (c) HBr, DMSO, 70 °C, 2 h, then pivalaldehyde, ammonium acetate, n-butanol, 50 °C, 2 h, 71%. (d) 11a: (i) diphenylmethanamine, dioxane, microwave 200 °C, 10 h, (ii) Pd/C, NH4OAc, MeOH, microwave 120–140 °C, 2 h, 28%. 11b: methylamine (2.0 M in THF), microwave 150 °C, 17 h, 18%. 11c: ammonium hydroxide, DMF, microwave 150 °C, 12 h, 85%. 11d: AcOH, H2O, microwave 190 °C, 2 h, 91%.