Scheme 1. Syntheses of Compounds 1–12.

Reagents and conditions: (a) arylboronic acid, 5 mol % Pd₂(dba)₃, 10 mol % PCy₃, 2M K₃PO₄, dioxane, 100 °C (microwave), 1 h, ca. 90%; (b) H₂SO₄/MeOH (1/10), 70 °C, 24 h, 91%; (c) H₂ (balloon), Pd/C, MeOH–acetone, 23 °C, 24 h, 92%; (d) 4-fluorobenzyl bromide, K₂CO₃, acetone, 70 °C, 5 h, 95%; (e) 10% NaOH (aq), MeOH/THF (1/1), 60 °C, 3 h, ca. 95%; (f) acetic anhydride, Et₃N, CH₂Cl₂, 0–23 °C, 1 h, 84%; (g) 10% NaOH (aq), MeOH/THF (1/1), 23 °C, 2 h, 36%; (h) 1-(aryl)piperazine, Pd(OAc)₂, P(o-tolyl)₃, Cs₂CO₃, toluene, 60 °C, 48 h, ca. 70%; (i) 13, 14, 15, 16, 17, 18, 19, 22b, 24b, 26b, 27b, 28b, or 29b (as appropriate), PyBOP, HOBt, Et₃N, CH₂Cl₂, 23 °C, 1 h, ca. 70%.