1: 2-(6-fluoro-1H-indol-3-yl)ethylamine tartrate With sodium hydroxide in tetrahydrofuran; toluene 2: 3-(2,2,3,3-tetrafluoropropoxy)benzaldehyde in isopropyl alcohol T=60°C; 2.5 h; 3: With sodium tetrahydroborate in isopropyl alcohol T=55°C; 2.5 h;

1.1: formic acid / water / 2 h / 80 °C / Reflux 1.2: 2 - 40 °C 1.3: 5 - 20 °C / pH > 14 2.1: N,N-dimethyl-formamide; water / 8 h / 100 - 105 °C 3.1: hydrogen; ammonia / water; methanol / 16 h / 60 °C / 1875.19 Torr 3.2: 0.25 h / Reflux 4.1: sodium hydroxide / toluene; tetrahydrofuran 4.2: 2.5 h / 60 °C 4.3: 2.5 h / 55 °C View Scheme

1.1: N,N-dimethyl-formamide; water / 8 h / 100 - 105 °C 2.1: hydrogen; ammonia / water; methanol / 16 h / 60 °C / 1875.19 Torr 2.2: 0.25 h / Reflux 3.1: sodium hydroxide / toluene; tetrahydrofuran 3.2: 2.5 h / 60 °C 3.3: 2.5 h / 55 °C View Scheme