Br[C:2]1[C:3]([Cl:8])=[N:4][CH:5]=[CH:6][CH:7]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.CC(C)([O-])C.[Na+].[NH:57]1[CH2:62][CH2:61][O:60][CH2:59][CH2:58]1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(C)C=CC=CC=1>[Cl:8][C:3]1[C:2]([N:57]2[CH2:62][CH2:61][O:60][CH2:59][CH2:58]2)=[CH:7][CH:6]=[CH:5][N:4]=1To a glass microwave vial was added 3-bromo-2-chloropyridine (0.5489 g, 2.85 mmol), Pd2(dba)3 (0.131 g, 0.143 mmol), xantphos (0.165 g, 0.285 mmol), and sodium tert-butoxide (0.524 mL, 4.28 mmol). The vial was capped and placed under vacuum for 5 minutes. Morpholine (0.248 mL, 2.85 mmol) and toluene (2 mL) were added. The reaction was allowed to stir at 100° C. Upon completion, the reaction was allowed to cool to room temperature. Solvent was evaporated. The crude product was adsorbed onto a plug of silica gel and chromatographed through a Biotage pre-packed silica gel column (25M), eluting with a gradient of 10% to 80% EtOAc in hexane, to provide 4-(2-chloropyridin-3-yl)morpholine. MS: [M+H]=199.0.
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