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Reagents and conditions: (a) 4-bromo-2-cyanopyridine, Pd(PPh3)4, K3PO4, dioxane, 90 °C (85%); (b) 1 M LiOH, THF, rt; (c) NH4Cl, EDC, HOBt, DIEA, 50 °C (77% over 2 steps); (d) dimethylformamide dimethyl acetal, 100 °C, then hydrazine, AcOH, 45 °C (68%); (e) CHIRALPAK OJ-H SFC 5 μM 21 × 250 mm column in 30% MeOH/CO2 at 60 mL/min.
