1: With anhydrous ammonium carbonate in N,N-dimethyl-formamide T=75 - 80°C; 5 h; 2: With hydrogenchloride in N,N-dimethyl-formamide

1: With 4-(N,N-dimethlyamino)pyridine in N,N-dimethyl-formamide 2: With (NH4)2CO3 in N,N-dimethyl-formamide T=75 - 80°C; 5 h; 3: With hydrogenchloride in water; N,N-dimethyl-formamide

1: 5-chloro-1-phenoxycarbonyl-2-(phenoxycarbonyloxy)indole With (NH4)2CO3 in N,N-dimethyl-formamide T=0 - 5°C; 5 h; 2: 2-thiophenoyl chloride With 4-(N,N-dimethlyamino)pyridine in N,N-dimethyl-formamide 3: With (NH4)2CO3 in N,N-dimethyl-formamide T=75 - 80°C; 5 h;

1: With anhydrous ammonium carbonate in N,N-dimethyl-formamide T=75 - 80°C; 5 h; 2: With hydrogenchloride in N,N-dimethyl-formamide

1.1: 53 percent / Et3N; 4-(dimethylamino)pyridine / dimethylformamide 2.1: 4-(dimethylamino)pyridine / dimethylformamide 2.2: 62 percent / HCl / dimethylformamide 3.1: ammonium carbonate / dimethylformamide / 5 h / 75 - 80 °C 3.2: 81 percent / HCl / dimethylformamide View Scheme

1.1: 4-(dimethylamino)pyridine / dimethylformamide 1.2: 62 percent / HCl / dimethylformamide 2.1: ammonium carbonate / dimethylformamide / 5 h / 75 - 80 °C 2.2: 81 percent / HCl / dimethylformamide View Scheme

1.1: ammonium carbonate / N,N-dimethyl-formamide / 0 - 20 °C 2.1: triethylamine / N,N-dimethyl-formamide / 1 h / 4 - 8 °C 2.2: 2 h / 5 °C 3.1: 4-(N,N-dimethlyamino)pyridine / N,N-dimethyl-formamide / 0 °C 3.2: 0.5 h / 5 °C 4.1: ammonium carbonate / dichloromethane / 4 h / |Reflux 5.1: ammonium carbonate / N,N-dimethyl-formamide / 5 h / 75 - 80 °C 5.2: 2 h / 0 - 5 °C View Scheme

1.1: triethylamine / tetrahydrofuran / 30 °C 2.1: ammonium carbonate / N,N-dimethyl-formamide / 0 - 20 °C 3.1: triethylamine / N,N-dimethyl-formamide / 1 h / 4 - 8 °C 3.2: 2 h / 5 °C 4.1: 4-(N,N-dimethlyamino)pyridine / N,N-dimethyl-formamide / 0 °C 4.2: 0.5 h / 5 °C 5.1: ammonium carbonate / dichloromethane / 4 h / |Reflux 6.1: ammonium carbonate / N,N-dimethyl-formamide / 5 h / 75 - 80 °C 6.2: 2 h / 0 - 5 °C View Scheme

1.1: N,N-dimethyl-formamide / 1 h / 4 - 8 °C 2.1: hydrogenchloride / N,N-dimethyl-formamide; water / 2 h / 5 °C 3.1: ammonium carbonate / dichloromethane / 4 h / |Reflux 4.1: ammonium carbonate / N,N-dimethyl-formamide / 5 h / 75 - 80 °C 4.2: 2 h / 0 - 5 °C View Scheme

1.1: Et3N; 4-(dimethylamino)pyridine / dimethylformamide 2.1: 4-(dimethylamino)pyridine / dimethylformamide 2.2: HCl / dimethylformamide 3.1: ammonium carbonate / dimethylformamide / 5 h / 75 - 80 °C 3.2: HCl / dimethylformamide View Scheme