Brc1ccccc1.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(c3ccccc3)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 bromobenzene (56.6 mg, 0.36 mmol) in toluene (5 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-phenyl-7-azaspiro[3.5]nonan-2-yl)methanone (59.0 mg, 46.8 %) as white solid. 1H NMR (400 MHz, CHLOROFORM- _d_ ) d ppm 1.60 - 1.75 (m, 4 H) 1.75 - 1.81 (m, 2 H) 1.81 - 1.95 (m, 2 H) 1.96 - 2.10 (m, 4 H) 2.10 - 2.20 (m, 2 H) 2.21 - 2.35 (m, 4 H) 2.71 (dq, _J_ =8.01, 7.75 Hz, 1 H) 3.00 - 3.11 (m, 2 H) 3.11 - 3.26 (m, 3 H) 3.31 - 3.42 (m, 2 H) 3.56 - 3.70 (m, 2 H) 6.82 (t, _J_ =7.23 Hz, 1 H) 6.93 (d, _J_ =7.81 Hz, 2 H) 7.18 - 7.29 (m, 2 H) HRMS _m/z_ calcd for C23H33N3O 368.26964 [M+H]+, found 368.26981. MS _m/z_ 368.3 [M+H]\+ (ES+)
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