N,N-dimethyl-aniline in xylene T=180°C; 2 h;

hydrogenchloride in ethanol T=80°C; Fischer indole synthesis; 6 h;

1: 1.) K2CO3 / 1.) THF, 1 h, 2.) THF, reflux, 24 h 2: 88 percent / tetrahydrofuran / 1.) -50 deg C, 4 h, 2.) r.t., 1 h 3: 88 percent / PDC / CH2Cl2 / 6 h / Heating 4: 97 percent / H2 / 5percent Pd/C / ethanol / 3 h / 760 Torr 5: 77 percent / pyridine / CH2Cl2 / 1 h / Ambient temperature 6: TiCl3/C8K / 1,2-dimethoxy-ethane / 1 h / Heating View Scheme

1: 88 percent / tetrahydrofuran / 1.) -50 deg C, 4 h, 2.) r.t., 1 h 2: 88 percent / PDC / CH2Cl2 / 6 h / Heating 3: 97 percent / H2 / 5percent Pd/C / ethanol / 3 h / 760 Torr 4: 77 percent / pyridine / CH2Cl2 / 1 h / Ambient temperature 5: TiCl3/C8K / 1,2-dimethoxy-ethane / 1 h / Heating View Scheme

1: 97 percent / H2 / 5percent Pd/C / ethanol / 3 h / 760 Torr 2: 77 percent / pyridine / CH2Cl2 / 1 h / Ambient temperature 3: TiCl3/C8K / 1,2-dimethoxy-ethane / 1 h / Heating View Scheme

1: 88 percent / PDC / CH2Cl2 / 6 h / Heating 2: 97 percent / H2 / 5percent Pd/C / ethanol / 3 h / 760 Torr 3: 77 percent / pyridine / CH2Cl2 / 1 h / Ambient temperature 4: TiCl3/C8K / 1,2-dimethoxy-ethane / 1 h / Heating View Scheme

titanium(III) chloride in ethylene glycol dimethyl ether 1 h; Heating;

1: 77 percent / pyridine / CH2Cl2 / 1 h / Ambient temperature 2: TiCl3/C8K / 1,2-dimethoxy-ethane / 1 h / Heating View Scheme

T=180°C;

1: 1.) Na/liquid NH3 / 1.) THF, -70 deg C, 30 min, 2.) THF, -70 deg C, 30 min 2: BBr3 / CH2Cl2 / -60 - 20 °C 3: pyridine / 2 h / Heating View Scheme