Br[C:2]1[CH:3]=[C:4]([CH:8]2[CH2:11][C:10]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]4[C:22]([C:29]5[C:34]([Cl:35])=[CH:33][CH:32]=[CH:31][C:30]=5[Cl:36])=[N:23][O:24][C:25]=4[CH:26]4[CH2:28][CH2:27]4)=[CH:15][C:14]=3[Cl:37])([OH:12])[CH2:9]2)[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.[CH3:80][N:81](C=O)C>O.[C-]#N.[C-]#N.[Zn+2].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]>[C:80]([C:2]1[CH:3]=[C:4]([CH:8]2[CH2:9][C:10]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]4[C:22]([C:29]5[C:30]([Cl:36])=[CH:31][CH:32]=[CH:33][C:34]=5[Cl:35])=[N:23][O:24][C:25]=4[CH:26]4[CH2:28][CH2:27]4)=[CH:15][C:14]=3[Cl:37])([OH:12])[CH2:11]2)[CH:5]=[CH:6][CH:7]=1)#[N:81]To a solution of compound 2b (3.1 g, 5 mmol) in DMF (50 mL) were added under argon atmosphere Zn(CN)2 (500 mg, 4.3 mmol), Pd2(dba)3 (300 mg, 0.33 mmol) and Xantphos (150 mg, 0.31 mmol). The mixture was stirred for 10 h at 115° C. under microwave irradiation. After cooling to rt the reaction mixture was diluted with water (250 mL) and extracted with EA (250 mL×2). The combined organic layers were washed with brine (100 mL×3) and dried over Na2SO4. The residue was purified by CC (EA/PE) to give the title compound 2c (1.2 g, 42%) as a pale yellow solid.
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