1: 4-bromo-1-chloroisoqionoline With n-butyllithium in tetrahydrofuran; hexane T=-78 - -68°C; Negishi Coupling Reaction; 0.5 h; 2: With zinc dibromide in tetrahydrofuran; hexane T=-78 - 20°C; Negishi Coupling Reaction; 0.666667 h; 3: 7-[(trifluoromethyl)sulfonyl]oxyisoquinoline With tetrakis(triphenylphosphine) palladium(0) in tetrahydrofuran; hexane T=20 - 60°C; Negishi Coupling Reaction; 0.5 h;

1.1: pyridine / ethyl acetate / 21.25 h / 0 - 22 °C / |Inert atmosphere; |Large scale 2.1: n-butyllithium / tetrahydrofuran; hexane / 0.67 h / -70 °C / |Inert atmosphere; |Large scale 2.2: 0.75 h / -70 - 0 °C / |Inert atmosphere; |Large scale 2.3: 1.67 h / 0 - 25 °C / |Inert atmosphere; |Large scale View Scheme

1.1: Na2WO4·2H2O; dihydrogen peroxide / acetic acid / 26 h / 80 °C / |Inert atmosphere; |Large scale 2.1: trichlorophosphate / N,N-dimethyl-formamide; toluene / 2 h / 5 - 20 °C / |Large scale 3.1: n-butyllithium / tetrahydrofuran; hexane / 0.67 h / -70 °C / |Inert atmosphere; |Large scale 3.2: 0.75 h / -70 - 0 °C / |Inert atmosphere; |Large scale 3.3: 1.67 h / 0 - 25 °C / |Inert atmosphere; |Large scale View Scheme

1.1: trichlorophosphate / N,N-dimethyl-formamide; toluene / 2 h / 5 - 20 °C / |Large scale 2.1: n-butyllithium / tetrahydrofuran; hexane / 0.67 h / -70 °C / |Inert atmosphere; |Large scale 2.2: 0.75 h / -70 - 0 °C / |Inert atmosphere; |Large scale 2.3: 1.67 h / 0 - 25 °C / |Inert atmosphere; |Large scale View Scheme