C1CCNCC1.CC(C)(C)OC(=O)c1ccc(Br)nc1>C1COCCO1.CC(=O)O.CC(=O)O.O=C([O-])[O-].[Cs+].[Cs+].[Pd].c1ccc(P(c2ccccc2)c2ccc3ccccc3c2-c2c(P(c3ccccc3)c3ccccc3)ccc3ccccc23)cc1>CC(C)(C)OC(=O)c1ccc(N2CCCCC2)nc1In a 100 mL round-bottomed flask was tert-butyl 6-bromonicotinate (516 mg, 2 mmol), piperidine (237 µl, 2.40 mmol), and CESIUM CARBONATE (977 mg, 3.00 mmol) in dioxane (9763 µl) to give a white suspension. The solution was degassed with N2 (g) fo 20 mins. PALLADIUM(II) ACETATE (22.45 mg, 0.10 mmol) and BINAP (62.3 mg, 0.10 mmol) were added under N2 (g) and the reaction was heated to 100 °C. Start Time: 01-Jul-10 1:10:32 PM -0400. The reaction was checked by LC-MS (complete), filtered, rinsed with DCM, concentrated in vacuo. _02 July 2010_ Purification by Iscos (25 g) using 100% Hexanes -> 50% EtOAc in Hexanes afforded a white solid. 325 mg obtained. 1H NMR (300 MHz, DMSO- _d_ 6) d ppm 1.51 - 1.57 (m, 12 H) 1.57 - 1.77 (m, 5 H) 3.58 - 3.74 (m, 4 H) 6.78 - 6.92 (m, 1 H) 7.88 (dd, _J_ =9.16, 2.36 Hz, 1 H) 8.60 (dd, _J_ =2.45, 0.57 Hz, 1 H). LC-MS: Rt = 2.37 min. Method: Short Purity. MS ES+: 263.2 [M+H]+.
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