1.1: 4-(N,N-dimethlyamino)pyridine; triethylamine / dichloromethane / 5 h / 20 °C 2.1: copper(l) iodide; potassium carbonate; sodium iodide / N,N-dimethyl-formamide / 24 h / 20 °C / Inert atmosphere 3.1: quinoline; hydrogen / ethyl acetate / 1 h / 20 °C / Inert atmosphere 4.1: lithium hydroxide hydrate / tetrahydrofuran / 16 h / 20 °C / Inert atmosphere 4.2: pH 2 / Inert atmosphere View Scheme

1.1: Jone's reagent / acetone / 0 - 20 °C 2.1: toluene-4-sulfonic acid / dichloromethane / 36 h / Reflux 3.1: copper(l) iodide; potassium carbonate; sodium iodide / N,N-dimethyl-formamide / 40 h / 20 °C / Inert atmosphere 4.1: phosphorus tribromide / diethyl ether / 20 °C / Inert atmosphere 5.1: copper(l) iodide; potassium carbonate; sodium iodide / N,N-dimethyl-formamide / 40 h / 20 °C / Inert atmosphere 6.1: phosphorus tribromide / diethyl ether / 20 °C / Inert atmosphere 7.1: copper(l) iodide; potassium carbonate; sodium iodide / N,N-dimethyl-formamide / 24 h / 20 °C / Inert atmosphere 8.1: quinoline; hydrogen / ethyl acetate / 1 h / 20 °C / Inert atmosphere 9.1: lithium hydroxide hydrate / tetrahydrofuran / 16 h / 20 °C / Inert atmosphere 9.2: pH 2 / Inert atmosphere View Scheme

1.1: toluene-4-sulfonic acid / dichloromethane / 36 h / Reflux 2.1: copper(l) iodide; potassium carbonate; sodium iodide / N,N-dimethyl-formamide / 40 h / 20 °C / Inert atmosphere 3.1: phosphorus tribromide / diethyl ether / 20 °C / Inert atmosphere 4.1: copper(l) iodide; potassium carbonate; sodium iodide / N,N-dimethyl-formamide / 40 h / 20 °C / Inert atmosphere 5.1: phosphorus tribromide / diethyl ether / 20 °C / Inert atmosphere 6.1: copper(l) iodide; potassium carbonate; sodium iodide / N,N-dimethyl-formamide / 24 h / 20 °C / Inert atmosphere 7.1: quinoline; hydrogen / ethyl acetate / 1 h / 20 °C / Inert atmosphere 8.1: lithium hydroxide hydrate / tetrahydrofuran / 16 h / 20 °C / Inert atmosphere 8.2: pH 2 / Inert atmosphere View Scheme

1.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere 2.1: 4-(N,N-dimethlyamino)pyridine; triethylamine / dichloromethane / 5 h / 20 °C 3.1: copper(l) iodide; potassium carbonate; sodium iodide / N,N-dimethyl-formamide / 24 h / 20 °C / Inert atmosphere 4.1: quinoline; hydrogen / ethyl acetate / 1 h / 20 °C / Inert atmosphere 5.1: lithium hydroxide hydrate / tetrahydrofuran / 16 h / 20 °C / Inert atmosphere 5.2: pH 2 / Inert atmosphere View Scheme

1.1: copper(l) iodide; potassium carbonate; sodium iodide / N,N-dimethyl-formamide / 40 h / 20 °C / Inert atmosphere 2.1: phosphorus tribromide / diethyl ether / 20 °C / Inert atmosphere 3.1: copper(l) iodide; potassium carbonate; sodium iodide / N,N-dimethyl-formamide / 40 h / 20 °C / Inert atmosphere 4.1: phosphorus tribromide / diethyl ether / 20 °C / Inert atmosphere 5.1: copper(l) iodide; potassium carbonate; sodium iodide / N,N-dimethyl-formamide / 24 h / 20 °C / Inert atmosphere 6.1: quinoline; hydrogen / ethyl acetate / 1 h / 20 °C / Inert atmosphere 7.1: lithium hydroxide hydrate / tetrahydrofuran / 16 h / 20 °C / Inert atmosphere 7.2: pH 2 / Inert atmosphere View Scheme

1.1: copper(l) iodide; potassium carbonate; sodium iodide / N,N-dimethyl-formamide / 24 h / 20 °C / Inert atmosphere 2.1: quinoline; hydrogen / ethyl acetate / 1 h / 20 °C / Inert atmosphere 3.1: lithium hydroxide hydrate / tetrahydrofuran / 16 h / 20 °C / Inert atmosphere 3.2: pH 2 / Inert atmosphere View Scheme

1.1: phosphorus tribromide / diethyl ether / 20 °C / Inert atmosphere 2.1: copper(l) iodide; potassium carbonate; sodium iodide / N,N-dimethyl-formamide / 40 h / 20 °C / Inert atmosphere 3.1: phosphorus tribromide / diethyl ether / 20 °C / Inert atmosphere 4.1: copper(l) iodide; potassium carbonate; sodium iodide / N,N-dimethyl-formamide / 24 h / 20 °C / Inert atmosphere 5.1: quinoline; hydrogen / ethyl acetate / 1 h / 20 °C / Inert atmosphere 6.1: lithium hydroxide hydrate / tetrahydrofuran / 16 h / 20 °C / Inert atmosphere 6.2: pH 2 / Inert atmosphere View Scheme

1.1: copper(l) iodide; potassium carbonate; sodium iodide / N,N-dimethyl-formamide / 40 h / 20 °C / Inert atmosphere 2.1: phosphorus tribromide / diethyl ether / 20 °C / Inert atmosphere 3.1: copper(l) iodide; potassium carbonate; sodium iodide / N,N-dimethyl-formamide / 24 h / 20 °C / Inert atmosphere 4.1: quinoline; hydrogen / ethyl acetate / 1 h / 20 °C / Inert atmosphere 5.1: lithium hydroxide hydrate / tetrahydrofuran / 16 h / 20 °C / Inert atmosphere 5.2: pH 2 / Inert atmosphere View Scheme

1.1: copper(l) iodide; potassium carbonate; sodium iodide / N,N-dimethyl-formamide / 24 h / 20 °C / Inert atmosphere 2.1: quinoline; hydrogen / ethyl acetate / 1 h / 20 °C / Inert atmosphere 3.1: lithium hydroxide hydrate / tetrahydrofuran / 16 h / 20 °C / Inert atmosphere 3.2: pH 2 / Inert atmosphere View Scheme

1.1: phosphorus tribromide / diethyl ether / 20 °C / Inert atmosphere 2.1: copper(l) iodide; potassium carbonate; sodium iodide / N,N-dimethyl-formamide / 24 h / 20 °C / Inert atmosphere 3.1: quinoline; hydrogen / ethyl acetate / 1 h / 20 °C / Inert atmosphere 4.1: lithium hydroxide hydrate / tetrahydrofuran / 16 h / 20 °C / Inert atmosphere 4.2: pH 2 / Inert atmosphere View Scheme