To a solution of 4-chloro-3-hydroxy-2-iodopyridine (1.04 g, 4.10 mmol) in DMF (10 mL) was added (Ph3P)2PdCl2 (0.140 g, 0.20 mmol), CuI (0.152 g, 0.80 mmol) and Et3N (0.496 g, 4.90 mmol). The mixture was stirred at room temperature for one hour. A solution of 1-Boc-2-(S)-ethynylpyrrolidine (0.80 g, 4.10 mmol), from step 1c above, in DMF (10 mL) was added and the mixture was heated at 60° C. for 16 hours. The reaction mixture was cooled to room temperature and poured into saturated NaHCO3 and washed with Et2O (4×100 mL). The combined organic extracts were washed with brine/H2O (1/1 400 mL), dried (MgSO4), and concentrated. The crude product was chromatographed (silica gel; CH2Cl2 /MeOH, 90:10) to afford the title compound as a brown oil (0.180 g, 14%): 1H NMR (CDCl3, 300 MHz) δ 1.40 (s, 9H), 1.95-2.10 (m, 4H), 3.10-3.25 (m, 2H), 4.90-5.10 (m, 1H), 6.65 (s, 1H), 7.10 (br s, 1H), 8.38 (br s, 1H); MS (DCI/NH3) m/z: 323 (M+H)+.
