C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.[Cl:47][C:48]1[C:53](I)=[CH:52][CH:51]=[CH:50][N:49]=1.C([O-])([O-])=O.[Cs+].[Cs+].[NH:61]1[CH2:66][CH2:65][O:64][CH2:63][CH2:62]1>CC([O-])=O.CC([O-])=O.[Pd+2].C1(C)C=CC=CC=1>[Cl:47][C:48]1[C:53]([N:61]2[CH2:66][CH2:65][O:64][CH2:63][CH2:62]2)=[CH:52][CH:51]=[CH:50][N:49]=1A 2-dram vial equipped with a stirbar was charged with Pd(OAc)2 (0.234 g, 1.044 mmol) and rac-BINAP (0.683 g, 1.096 mmol) as solids. Toluene (4 mL) was added via syringe, and the mixture was stirred for 10 min while being degassed with argon, and until a uniform tan suspension resulted. A 100-mL round-bottom flask was charged with 2-chloro-3-iodopyridine (1.25 g, 5.22 mmol) and Cs2CO3 (7.14 g, 21.93 mmol). Toluene (34.8 mL) was added followed by morpholine (0.542 ml, 6.26 mmol). This solution was degassed for 1 min under argon, and then the catalyst/ligand suspension was added via pasteur pipette. A reflux condenser was attached to the flask, and the reaction mixture was refluxed at 120° C. for 16 h. The reaction mixture was concentrated in vacuo, and then diluted with CH2Cl2 (150 mL). The organics were washed with 2×100 mL brine, dried over Na2SO4, filtered, and concentrated in vacuo. The material was purified by gradient elution on silica gel (5 to 75% [5% MeOH/EtOAc] in hexanes) to afford the title compound as light yellow solid (700 mg, 64%). Data for 2-1: 1H NMR (500 MHz, CDCl3) d 8.08 (dd, J=4.4, 1.5 Hz, 1H), 7.32 (dd, J=7.8, 1.5 Hz, 1H), 7.21 (dd, J=7.8, 4.5 Hz, 1H), 3.89 (dd, J=4.5, 4.5 Hz, 4H), 3.08 (dd, J=4.5, 4.5 Hz, 4H); HRMS m/z (M+H) 199.0630 found, 199.0633 required.
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