[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([NH2:11])([CH3:10])[CH3:9])=[CH:4][C:3]=1[CH3:12].CC(C)([O-])C.[K+].[I:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22](I)[CH:21]=1.CCOCC>COCCOC>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([NH:11][C:22]2[CH:23]=[CH:24][CH:25]=[C:20]([I:19])[CH:21]=2)([CH3:9])[CH3:10])=[CH:4][C:3]=1[CH3:12]A suspension of amine INT 22 (2.8 g, 15.24 mmol) and potassium tert-butoxide (5.99 g, 53.4 mmol) in DME (25 mL) was purged with argon for 5 minutes. Then, PEPPSI-IPr® (207 mg, 0.305 mmol) and 1,3-diiodobenzene (5.03 g, 15.24 mmol) were added and the flask was closed. The mixture was stirred at room temperature over the weekend. The crude reaction mixture was treated with Et2O (50 mL) and filtered. The residue was washed with more Et2O (30 mL) and the combined filtrates were concentrated. The crude was purified by chromatography on silica gel (cyclohexane/CH2Cl2).
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