1: (5-fluoroindol-3-yl)carboxaldehyde With sodium tetrahydroborate in methanol; formamide 0.5 h; 2: potassium cyanide in methanol; formamide T=100°C; 1 h;

sodium hydroxide; formaldehyd; tetrabutyl ammonium fluoride; acetic acid; dimethyl amine in tetrahydrofuran; dichloromethane; water; ethyl acetate; toluene

potassium cyanide in methanol; water

in tetrahydrofuran; water Substitution; MeI adding to a pre-cooled indole (5 deg C) in THF; stirring overnight; aq. KCN adding; stirring at reflux under Ar;

1: 98 percent / AcOH / 17.5 h / 6 - 21 °C / Et2NH in AcOH and 30 min after aq. CH2O mixing at 6 deg C; pouring into a pre-cooled indole; quenching with 10 percent NaOH 2: 90 percent / tetrahydrofuran; H2O / MeI adding to a pre-cooled indole (5 deg C) in THF; stirring overnight; aq. KCN adding; stirring at reflux under Ar View Scheme

in methanol; formamide T=100°C; 2.5 h;

20percent KOH in water 5 h; Heating;