[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Br[C:8]1[CH:20]=[CH:19][CH:18]=[CH:17][C:9]=1[C:10]([N:12]([CH2:15][CH3:16])[CH2:13][CH3:14])=[O:11].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.C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH2:15]([N:12]([CH2:13][CH3:14])[C:10]([C:9]1[CH:17]=[CH:18][CH:19]=[CH:20][C:8]=1[N:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1)=[O:11])[CH3:16]Piperazine (489 mg, 4.8 mmol), 2-bromo-N,N-diethyl-benzamide (1 g, 3.95 mmol), Pd2(dba)3 (235 mg, 0.2 mmol), BINAP (442 mg, 0.6 mmol), and cesium carbonate (3 g, 5.53 mmol) were mixed together in toluene (20 mL). The mixture was degassed and heated to 100° C. for about 72 hours. The mixture was diluted with ether (100 mL) and filtered over celite. The filtrate was concentrated and then subjected to chromatography on silica gel to give the title compound (480 mg, 47%) as a brown oil. LRMS (ESI+): 262.2 (M+1)
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