Brc1ccccn1.O=C(C1CC2(CCNCC2)C1)N1CCN(C2CCC2)CC1>CC(=O)O.CC(=O)O.Cc1ccccc1.O=C([O-])[O-].[Cs+].[Cs+].[Pd].c1ccc(P(c2ccccc2)c2ccc3ccccc3c2-c2c(P(c3ccccc3)c3ccccc3)ccc3ccccc23)cc1>O=C(C1CC2(CCN(c3ccccn3)CC2)C1)N1CCN(C2CCC2)CC1cesium carbonate (123 mg, 0.38 mmol) was added to a solution of (4-cyclobutylpiperazin-1-yl)(7-azaspiro[3.5]nonan-2-yl)methanone (100 mg, 0.34 mmol), PdOAc2 (7.70 mg, 0.03 mmol), BINAP (42.7 mg, 0.07 mmol) and 2-bromopyridine (56.9 mg, 0.36 mmol) in toluene (2 mL). The reaction mixture was heated to 110°C for 18hrs. The room temperature cooled down mixture was filtered over celite. The solvent was concentrated. The product was purified by preparative HPLC using a low pH shallow gradient method (Mobile phase: 20-40% B; A: H2O with 0.05% TFA , B: CH3CN, 25 min. run) on Luna 15 m, C8 (2), 21.2x250 mm Phenomenex reverse phase column to provide (4-cyclobutylpiperazin-1-yl)(7-(pyridin-2-yl)-7-azaspiro[3.5]nonan-2-yl)methanone (54.1 mg, 42.8 %) as white solid. 1H NMR (400 MHz, CHLOROFORM- _d_ ) d ppm 1.62 - 1.75 (m, 4 H) 1.75 - 1.81 (m, 2 H) 1.81 - 1.94 (m, 2 H) 1.98 - 2.10 (m, 4 H) 2.12 - 2.21 (m, 2 H) 2.23 - 2.32 (m, 4 H) 2.71 (quin, _J_ =7.91 Hz, 1 H) 3.05 - 3.14 (m, 2 H) 3.14 - 3.26 (m, 3 H) 3.33 - 3.40 (m, 2 H) 3.58 - 3.68 (m, 2 H) 7.09 - 7.15 (m, 1 H) 7.16 - 7.21 (m, 1 H) 8.06 (dd, _J_ =4.49, 1.37 Hz, 1 H) 8.31 (d, _J_ =2.73 Hz, 1 H) HRMS _m/z_ calcd for C22H32N4O 369.26489 [M+H]+, found 369.26461 . MS _m/z_ 369.2 [M+H]\+ (ES+)
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