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Conditions: (i) K2CO3, DMF, 60 °C, 16 h, 70% for 8a; K2CO3, acetone, 70 °C, 5 h for 8b; (ii) ICI, CH2Cl2/MeOH, rt, 10 min, 83% for 9a; (iii) 4-pyridylboronic acid, Cs2CO3, Pd(PPh3)4, dioxane/H2O, 110 °C, 2 h, 33% (or 19% overall yield from 5) for 10 and 29% overall yield from 5 for 4; (iv) NaOMe, MeOH, 0 °C, 20 min, 62%; (v) Pt(PEt3)2(OTf)2, CH2Cl2/MeCN (4:1), 60 °C, 24 h, 73% for 1 and 70% for 2.
