1: 43 percent / butan-1-ol / 24 h / 90 °C 2: 84.5 percent / PPh3, DEAD / tetrahydrofuran / Ambient temperature 3: 71 percent / H2, phosphoric acid, KOH / Pd/C / H2O; tetrahydrofuran / 6 h / 0 - 55 °C / 760 Torr 4: 88.8 percent / Br2, NaOAc / acetic acid / Ambient temperature 5: 80 percent / K2CO3 / acetonitrile / 75 °C 6: 75.7 percent / various solvent(s) / 2.5 h / 200 °C 7: 94.5 percent / n-BuLi / tetrahydrofuran / -65 °C 8: 23.53 g / PPA / 2 h / 85 - 90 °C 9: 62 percent / MnO2 / CH2Cl2; acetic acid / 5.5 h / -10 °C / other reagent, solvent, temperature, reaction time View Scheme

1: (6-bromo-1,3,4,5-tetrahydro-benzo[cd]indol-4-yl)-dipropyl-amine With tert.-butyl lithium; potassium hydride in diethyl ether; pentane T=-78 - -40°C; 2: trimethylsilyl isocyanate in diethyl ether; pentane T=-78 - -10°C;

palladium on activated charcoal in methanol; sulfuric acid; water T=80°C; 7 h;

1: 88.8 percent / Br2, NaOAc / acetic acid / Ambient temperature 2: 80 percent / K2CO3 / acetonitrile / 75 °C 3: 75.7 percent / various solvent(s) / 2.5 h / 200 °C 4: 94.5 percent / n-BuLi / tetrahydrofuran / -65 °C 5: 23.53 g / PPA / 2 h / 85 - 90 °C 6: 62 percent / MnO2 / CH2Cl2; acetic acid / 5.5 h / -10 °C / other reagent, solvent, temperature, reaction time View Scheme

1: H2 / 10percent Pd/C 2: 88 percent / DEAD, Ph3P / or with Br2/Ph3P 3: 90 percent / H2 / 10percent Pd/C / acetic acid / 760 Torr / 0 to 55 deg C 4: 89 percent / Br2, NaOAc / acetic acid 5: 80 percent / K2CO3 / acetonitrile / 80 °C 6: 76 percent / various solvent(s) / 200 °C 7: 95 percent / n-BuLi / low temperature 8: 83 percent / MnO2 / acetic acid / 10 °C 9: polyphosphoric acid View Scheme

1: 23.53 g / PPA / 2 h / 85 - 90 °C 2: 62 percent / MnO2 / CH2Cl2; acetic acid / 5.5 h / -10 °C / other reagent, solvent, temperature, reaction time View Scheme

1: 80 percent / K2CO3 / acetonitrile / 75 °C 2: 75.7 percent / various solvent(s) / 2.5 h / 200 °C 3: 94.5 percent / n-BuLi / tetrahydrofuran / -65 °C 4: 23.53 g / PPA / 2 h / 85 - 90 °C 5: 62 percent / MnO2 / CH2Cl2; acetic acid / 5.5 h / -10 °C / other reagent, solvent, temperature, reaction time View Scheme

1: 75.7 percent / various solvent(s) / 2.5 h / 200 °C 2: 94.5 percent / n-BuLi / tetrahydrofuran / -65 °C 3: 23.53 g / PPA / 2 h / 85 - 90 °C 4: 62 percent / MnO2 / CH2Cl2; acetic acid / 5.5 h / -10 °C / other reagent, solvent, temperature, reaction time View Scheme

1: 94.5 percent / n-BuLi / tetrahydrofuran / -65 °C 2: 23.53 g / PPA / 2 h / 85 - 90 °C 3: 62 percent / MnO2 / CH2Cl2; acetic acid / 5.5 h / -10 °C / other reagent, solvent, temperature, reaction time View Scheme

1: 91 percent / NaOH / tetrahydrofuran; H2O / 3 h / Heating 2: 88.8 percent / Br2, NaOAc / acetic acid / Ambient temperature 3: 80 percent / K2CO3 / acetonitrile / 75 °C 4: 75.7 percent / various solvent(s) / 2.5 h / 200 °C 5: 94.5 percent / n-BuLi / tetrahydrofuran / -65 °C 6: 23.53 g / PPA / 2 h / 85 - 90 °C 7: 62 percent / MnO2 / CH2Cl2; acetic acid / 5.5 h / -10 °C / other reagent, solvent, temperature, reaction time View Scheme