sodium carbonate; [1,4-bis-(diphenylphosphine)butane]palladium (II) dichloride in ethylene glycol dimethyl ether; ethanol; water T=90°C; 2.5 h; Inert atmosphere;

hydrogen; nickel in ethanol 1.5 h; Heating;

1: With sodium hydroxide; iron(III) chloride in methanol 4 h; Heating; 2: With hydrogen; palladium on activated charcoal T=50°C; P=3800 Torr; 18 h;

potassium phosphate; tetrakis(triphenylphosphine) palladium(0) in 1,4-dioxane T=80°C; Suzuki-Miyaura coupling;

hydrogenchloride in ethanol; water

1: 69 percent / hydroxybenzotriazole; EDC; pyridine / CH2Cl2 / 15 h / 20 °C 2: CH2Cl2 / 1.5 h / 0 °C 3: NH2OH*HCl; Na2CO3 / ethanol; H2O / 19 h / 20 - 70 °C 4: H2 / Raney-Ni W2 / methanol / 3 h / 20 °C / atmospheric pressure 5: pyridine / 1 h / 20 °C 6: 91 percent / NaH / tetrahydrofuran / 2 h / 20 °C 7: 85 percent / i-Pr2NEt / CH2Cl2 / 2 h / 0 °C 8: 85 percent / K3PO4*3H2O; Pd(PPh3)4 / dioxane / 1.5 h / 80 °C 9: 38 percent / H2SO4 / 0.17 h / 0 °C View Scheme

1: 96 percent / cc. H2SO4 / 0.5 h / 0 °C 2: 82 percent / K3PO4 / Pd(PPh3)4 / dioxane / 80 °C View Scheme

sulfuric acid T=0°C; 0.166667 h;

1: H2 / Raney-Ni W2 / methanol / 3 h / 20 °C / atmospheric pressure 2: pyridine / 1 h / 20 °C 3: 91 percent / NaH / tetrahydrofuran / 2 h / 20 °C 4: 85 percent / i-Pr2NEt / CH2Cl2 / 2 h / 0 °C 5: 85 percent / K3PO4*3H2O; Pd(PPh3)4 / dioxane / 1.5 h / 80 °C 6: 38 percent / H2SO4 / 0.17 h / 0 °C View Scheme

1: CH2Cl2 / 1.5 h / 0 °C 2: NH2OH*HCl; Na2CO3 / ethanol; H2O / 19 h / 20 - 70 °C 3: H2 / Raney-Ni W2 / methanol / 3 h / 20 °C / atmospheric pressure 4: pyridine / 1 h / 20 °C 5: 91 percent / NaH / tetrahydrofuran / 2 h / 20 °C 6: 85 percent / i-Pr2NEt / CH2Cl2 / 2 h / 0 °C 7: 85 percent / K3PO4*3H2O; Pd(PPh3)4 / dioxane / 1.5 h / 80 °C 8: 38 percent / H2SO4 / 0.17 h / 0 °C View Scheme