[C:1]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13](Br)[CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(C)CCN.[I-:25].[Na+]>O1CCOCC1.N.[Cu]I>[C:1]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([I:25])[CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]
To 13.0 g (41.6 mmol) 6-bromo-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester in 42 mL 1,4-dioxane is added 817 mg (4.21 mmol) copper(I)-iodide under argon. After flushing with argon, 0.89 mL (8.33 mmol) N,N-dimethylethylen-diamine and 12.5 g (83.3 mmol) sodium iodide is added at RT. The reaction mixture is stirred 14 h at 110° C., is cooled to RT and is diluted with 5% aqueous ammonia-solution. The layers are separated and the aqueous phase is extracted with EtOAc. The combined organic phase is washed with water and is dried over MgSO4, filtered and the solvent is evaporated to give the product.
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