caesium carbonate; palladium dichloride in N,N-dimethyl-formamide T=80°C; Suzuki-Miyaura Coupling; 6 h; Inert atmosphere;

in water; acetone T=20 - 75°C; 18.5 h; Heating / reflux;

ammonia; triethylamine in dichloromethane; water; ethyl acetate

copper(l) iodide; palladium diacetate; potassium carbonate; triphenylphosphine in ethylene glycol dimethyl ether T=70 - 95°C; Suzuki coupling; 5.5 h; Inert atmosphere;

1.1: 3 h / 60 °C / Inert atmosphere 2.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 3 h / 120 °C / Inert atmosphere 3.1: water; hydrogen bromide / 3 h / 110 °C 3.2: pH 11 / Cooling with ice 4.1: pyridine; copper diacetate / N,N-dimethyl-formamide / 16 h 5.1: N-bromosuccinmide / N,N-dimethyl-formamide / 4 h / 20 °C 6.1: copper(l) iodide; palladium diacetate; potassium carbonate; triphenylphosphine / ethylene glycol dimethyl ether / 5.5 h / 70 - 95 °C / Inert atmosphere View Scheme

1.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 3 h / 120 °C / Inert atmosphere 2.1: water; hydrogen bromide / 3 h / 110 °C 2.2: pH 11 / Cooling with ice 3.1: pyridine; copper diacetate / N,N-dimethyl-formamide / 16 h 4.1: N-bromosuccinmide / N,N-dimethyl-formamide / 4 h / 20 °C 5.1: copper(l) iodide; palladium diacetate; potassium carbonate; triphenylphosphine / ethylene glycol dimethyl ether / 5.5 h / 70 - 95 °C / Inert atmosphere View Scheme

1: pyridine; copper diacetate / N,N-dimethyl-formamide / 16 h 2: N-bromosuccinmide / N,N-dimethyl-formamide / 4 h / 20 °C 3: copper(l) iodide; palladium diacetate; potassium carbonate; triphenylphosphine / ethylene glycol dimethyl ether / 5.5 h / 70 - 95 °C / Inert atmosphere View Scheme

1.1: water; hydrogen bromide / 3 h / 110 °C 1.2: pH 11 / Cooling with ice 2.1: pyridine; copper diacetate / N,N-dimethyl-formamide / 16 h 3.1: N-bromosuccinmide / N,N-dimethyl-formamide / 4 h / 20 °C 4.1: copper(l) iodide; palladium diacetate; potassium carbonate; triphenylphosphine / ethylene glycol dimethyl ether / 5.5 h / 70 - 95 °C / Inert atmosphere View Scheme

1.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 3 h / 120 °C / Inert atmosphere 2.1: water; hydrogen bromide / 3 h / 110 °C 2.2: pH 11 / Cooling with ice 3.1: pyridine; copper diacetate / N,N-dimethyl-formamide / 16 h 4.1: N-bromosuccinmide / N,N-dimethyl-formamide / 4 h / 20 °C 5.1: copper(l) iodide; palladium diacetate; potassium carbonate; triphenylphosphine / ethylene glycol dimethyl ether / 5.5 h / 70 - 95 °C / Inert atmosphere View Scheme

1: pyridine; copper diacetate / N,N-dimethyl-formamide / 16 h 2: N-bromosuccinmide / N,N-dimethyl-formamide / 4 h / 20 °C 3: copper(l) iodide; palladium diacetate; potassium carbonate; triphenylphosphine / ethylene glycol dimethyl ether / 5.5 h / 70 - 95 °C / Inert atmosphere View Scheme