4-(N,N-dimethlyamino)pyridine; dicyclohexyl-carbodiimide in dichloromethane T=25 - 35°C;

4-methyl-morpholine in dichloromethane T=25 - 35°C; 0.5 h; Inert atmosphere;

1: 45 percent / silver(I) oxide / dioxane / 20 h / 60 °C 2: 1.) NaH / 1.) THF, 10 min, 2.) 30 min 3: 98 percent / H2 / 10percent Pd/C / tetrahydrofuran / 2 h / 2587.7 Torr 4: 74 percent / N-methylmorpholine / CH2Cl2 / 2 h 5: 88 percent / LiOH monohydrate / methanol; tetrahydrofuran; H2O / 20 h 6: 69 percent / 4-(dimethylamino)pyridine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / CH2Cl2 / 18 h View Scheme

1: 1.) NaH / 1.) THF, 10 min, 2.) 30 min 2: 98 percent / H2 / 10percent Pd/C / tetrahydrofuran / 2 h / 2587.7 Torr 3: 74 percent / N-methylmorpholine / CH2Cl2 / 2 h 4: 88 percent / LiOH monohydrate / methanol; tetrahydrofuran; H2O / 20 h 5: 69 percent / 4-(dimethylamino)pyridine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / CH2Cl2 / 18 h View Scheme

1: 98 percent / H2 / 10percent Pd/C / tetrahydrofuran / 2 h / 2587.7 Torr 2: 74 percent / N-methylmorpholine / CH2Cl2 / 2 h 3: 88 percent / LiOH monohydrate / methanol; tetrahydrofuran; H2O / 20 h 4: 69 percent / 4-(dimethylamino)pyridine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / CH2Cl2 / 18 h View Scheme

1: 45 percent / silver(I) oxide / dioxane / 20 h / 60 °C 2: 1.) NaH / 1.) THF, 10 min, 2.) 30 min 3: 98 percent / H2 / 10percent Pd/C / tetrahydrofuran / 2 h / 2587.7 Torr 4: 74 percent / N-methylmorpholine / CH2Cl2 / 2 h 5: 88 percent / LiOH monohydrate / methanol; tetrahydrofuran; H2O / 20 h 6: 69 percent / 4-(dimethylamino)pyridine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / CH2Cl2 / 18 h View Scheme

1: 74 percent / N-methylmorpholine / CH2Cl2 / 2 h 2: 88 percent / LiOH monohydrate / methanol; tetrahydrofuran; H2O / 20 h 3: 69 percent / 4-(dimethylamino)pyridine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / CH2Cl2 / 18 h View Scheme

1: 74 percent / N-methylmorpholine / CH2Cl2 / 2 h 2: 88 percent / LiOH monohydrate / methanol; tetrahydrofuran; H2O / 20 h 3: 69 percent / 4-(dimethylamino)pyridine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / CH2Cl2 / 18 h View Scheme

1: 88 percent / LiOH monohydrate / methanol; tetrahydrofuran; H2O / 20 h 2: 69 percent / 4-(dimethylamino)pyridine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / CH2Cl2 / 18 h View Scheme

1: 1-methyl-5-nitro-1H-indole; 3-methoxy-4-bromomethyl-benzoic acid methyl ester With copper(I) oxide in 1,4-dioxane T=95 - 100°C; Friedel Crafts alkylation; Large scale reaction; 2: With hydrogen in ethyl acetate T=25 - 30°C; P=3677.86 - 4413.43 Torr; Large scale reaction; 3: 2-toluenesulfonamide; cyclopentyl Chloroformate Further stages;