1.1: 99 percent / aq. NaOH / Heating 2.1: 87 percent / Cu; quinoline / Heating 3.1: 89 percent / phosphoryl chloride / 0 - 40 °C 4.1: NaOH / CH2Cl2 / 20 °C 4.2: 97 percent / CH2Cl2 / 20 °C View Scheme

1.1: 99 percent / aq. NaOH / Heating 2.1: 87 percent / Cu; quinoline / Heating 3.1: 89 percent / phosphoryl chloride / 0 - 40 °C 4.1: NaOH / CH2Cl2 / 20 °C 4.2: 97 percent / CH2Cl2 / 20 °C 5.1: n-BuLi / tetrahydrofuran; hexane / 0 °C 5.2: potassium tert-butoxide / tetrahydrofuran; hexane / 0 °C 5.3: 91 percent / tetrahydrofuran; hexane / -78 - 0 °C 6.1: 80 percent / H2 / Pd/C / ethanol / 20 °C / 760 Torr View Scheme

1.1: 99 percent / aq. NaOH / Heating 2.1: 87 percent / Cu; quinoline / Heating 3.1: 89 percent / phosphoryl chloride / 0 - 40 °C 4.1: NaOH / CH2Cl2 / 20 °C 4.2: 97 percent / CH2Cl2 / 20 °C 5.1: n-BuLi / tetrahydrofuran; hexane / 0 °C 5.2: potassium tert-butoxide / tetrahydrofuran; hexane / 0 °C 5.3: 78 percent / tetrahydrofuran; hexane / -78 - 0 °C 6.1: 85 percent / H2 / Pd/C / ethanol / 20 °C / 760 Torr View Scheme

1: With benzene diazonium chloride; sodium carbonate in N,N-dimethyl-formamide T=0 - 5°C; pH=8.0 - 9.0; 30 h; 2: With hydrogenchloride; tin in water; isopropyl alcohol 2 h; Heating;

sodium hydride in N,N-dimethyl-formamide T=0 - 20°C; 15 h;

1: 88 percent / NaH / dimethylformamide / 15 h / 0 - 20 °C 2: 98 percent / LiOH*H2O / ethanol / 18 h / Heating View Scheme

1: N,N-dimethyl-formamide With trichlorophosphate in dichloromethane T=0°C; 0.5 h; 2: 6-methoxy-1H-indole-2-carboxylic acid methyl ester in dichloromethane T=0°C; Vilsmeier formylation; 0.5 h; Further stages.;