Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[CH:3]=1.[NH:9]1[CH2:19][CH2:18][CH:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:11][CH2:10]1.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.CC([O-])(C)C.[Na+]>C1(C)C=CC=CC=1.O.C(OCC)(=O)C.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]>[Br:8][C:4]1[CH:3]=[C:2]([N:9]2[CH2:19][CH2:18][CH:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:11][CH2:10]2)[CH:7]=[CH:6][CH:5]=1To a solution of 1,3-dibromobenzene (10 g, 42 mmol) in toluene (424 mL), were added ethyl isonipecotate (6.5 mL, 42 mmol), rac-BINAP (2.0 g, 3.2 mmol), NaOtBu (4.9 g, 51 mmol) and Pd2(dba)3 (0.97 g, 1.1 mmol). The mixture was heated at 80° C. for 4 h and diluted with water and ethyl acetate and separated. The organic phase was dried over unhydrous Na2SO4 and evaporated under reduced pressure. The residue was purified with silica gel column chromatography (hexane/ethyl acetate 10:0 to 9:1) to give the titled compound (5.6 g, 42%).
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