Multi-step reaction with 12 steps
1.1: diisopropylamine; n-butyllithium / tetrahydrofuran / 1 h / Cooling with hexane-dry ice; Inert atmosphere
1.2: 0.5 h / -60 °C / Cooling with hexane-dry ice; Inert atmosphere
2.1: boron trifluoride diethyl etherate / tetrahydrofuran / Cooling with ice
3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.58 h / Inert atmosphere; Cooling with ice
4.1: 1,4-dioxane / 17 h / 94 °C
5.1: toluene-4-sulfonic acid / 1 h / 56 °C
6.1: morpholine / ethyl acetate / 3 h / 74 °C
7.1: lithium hexamethyldisilazane; iodine / tetrahydrofuran / 2 h / -60 °C / Cooling with hexane-dry ice; Inert atmosphere
8.1: potassium phosphate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,2-dimethoxyethane / 1 h / 80 °C
9.1: sodium hydroxide; water / 1,4-dioxane / 17 h / 20 - 100 °C
9.2: Cooling with ice
10.1: triethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 1 h / 20 °C
11.1: trifluoroacetic acid / 6 h / 80 °C
12.1: water; lithium hydroxide / isopropyl alcohol / 1 h / 20 - 70 °C
12.2: 70 °C / Cooling
With
morpholine; potassium phosphate; n-butyllithium; boron trifluoride diethyl etherate; water; iodine; sodium hydride; benzotriazol-1-ol; toluene-4-sulfonic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; diisopropylamine; trifluoroacetic acid; sodium hydroxide; lithium hydroxide; lithium hexamethyldisilazane;
dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2;
In
tetrahydrofuran; 1,4-dioxane; 1,2-dimethoxyethane; ethyl acetate; N,N-dimethyl-formamide; isopropyl alcohol; mineral oil;