1.1: 94 percent / Cu; quinoline / 2 h / Heating 2.1: 85 percent / phosphoryl chloride / 1.5 h / 0 - 40 °C 3.1: NaOH / CH2Cl2 / 0.5 h / 20 °C 3.2: 97 percent / CH2Cl2 / 12 h / 20 °C View Scheme

1.1: 94 percent / Cu; quinoline / 2 h / Heating 2.1: 85 percent / phosphoryl chloride / 1.5 h / 0 - 40 °C 3.1: NaOH / CH2Cl2 / 0.5 h / 20 °C 3.2: 97 percent / CH2Cl2 / 12 h / 20 °C 4.1: n-BuLi / tetrahydrofuran; hexane / 0.25 h / 0 °C 4.2: potassium tert-butoxide / tetrahydrofuran; hexane / 0.25 h / 0 °C 4.3: 74 percent / tetrahydrofuran; hexane / 2.5 h / -78 - 0 °C 5.1: 93 percent / H2 / Pd/C / ethanol / 4 h / 20 °C / 760 Torr View Scheme

1.1: 94 percent / Cu; quinoline / 2 h / Heating 2.1: 85 percent / phosphoryl chloride / 1.5 h / 0 - 40 °C 3.1: NaOH / CH2Cl2 / 0.5 h / 20 °C 3.2: 97 percent / CH2Cl2 / 12 h / 20 °C 4.1: n-BuLi; potassium tert-butoxide / tetrahydrofuran; hexane / 0 °C 4.2: 71 percent / tetrahydrofuran; hexane / -78 - 0 °C 5.1: 94 percent / H2 / Pd/C / ethanol / 20 °C / 760 Torr View Scheme

1.1: 94 percent / Cu; quinoline / 2 h / Heating 2.1: 85 percent / phosphoryl chloride / 1.5 h / 0 - 40 °C 3.1: NaOH / CH2Cl2 / 0.5 h / 20 °C 3.2: 97 percent / CH2Cl2 / 12 h / 20 °C 4.1: n-BuLi / tetrahydrofuran; hexane / 0 °C 4.2: potassium tert-butoxide / tetrahydrofuran; hexane / 0 °C 4.3: 45 percent / tetrahydrofuran; hexane / -78 - 0 °C 5.1: 57 percent / H2 / Pd/C / ethanol / 20 °C / 760 Torr View Scheme

1.1: 94 percent / Cu; quinoline / 2 h / Heating 2.1: 85 percent / phosphoryl chloride / 1.5 h / 0 - 40 °C 3.1: NaOH / CH2Cl2 / 0.5 h / 20 °C 3.2: 97 percent / CH2Cl2 / 12 h / 20 °C 4.1: n-BuLi / tetrahydrofuran; hexane / 0 °C 4.2: potassium tert-butoxide / tetrahydrofuran; hexane / 0 °C 4.3: 69 percent / tetrahydrofuran; hexane / -78 - 0 °C 5.1: 47 percent / H2 / Pd/C / ethanol / 20 °C / 760 Torr View Scheme

1.1: 94 percent / Cu; quinoline / 2 h / Heating 2.1: 85 percent / phosphoryl chloride / 1.5 h / 0 - 40 °C 3.1: NaOH / CH2Cl2 / 0.5 h / 20 °C 3.2: 97 percent / CH2Cl2 / 12 h / 20 °C 4.1: n-BuLi / tetrahydrofuran; hexane / 0 °C 4.2: potassium tert-butoxide / tetrahydrofuran; hexane / 0 °C 4.3: 68 percent / tetrahydrofuran; hexane / -78 - 0 °C 5.1: 50 percent / H2 / Pd/C / ethanol / 20 °C / 760 Torr View Scheme

hydrogenchloride