Scheme 3.
Reagents and conditions: (a) Br2, 80% aq. acetic acid, Fe, 20 °C; (b) MOM-Cl, Cs2CO3, ACN, reflux, 2–3 h; (c) 3- or 4-pyridine boronic acid, Pd(PPh3)4, toluene, EtOH, K2CO3 aq. (2 M), reflux, overnight; (d) 10% HCl aq. in MeOH (1:9), 50 °C, overnight; (e) NaBH4, MeOH/DCM (9:1), 0 °C, 2–3 h.