Multi-step reaction with 11 steps
1.1: iron; ammonium chloride / ethanol; water / 2 h / 78 °C
2.1: n-Butyl nitrite; copper(I) bromide / acetonitrile / 18 h / 20 °C
3.1: ammonium acetate; acetic acid / 18 h / 80 °C
4.1: sodium tetrahydroborate; borane-THF / tetrahydrofuran / 18 h / 0 - 65 °C / Inert atmosphere
5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere
6.1: trichlorophosphate / toluene / 2 h / 110 °C
7.1: potassium carbonate; triethylamine / acetonitrile / 2 h / 100 °C
8.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / 1,4-dioxane; water / 1.75 h / 85 °C / Inert atmosphere; Sealed tube
9.1: water; sodium hydroxide / ethanol / 3 h / 75 °C
9.2: pH 1
10.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 18 h
11.1: palladium diacetate; caesium carbonate; triphenylphosphine / 1,4-dioxane / 22.5 h / Inert atmosphere; Sealed tube
11.2: 2 h
With
(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium tetrahydroborate; borane-THF; n-Butyl nitrite; ammonium acetate; water; palladium diacetate; iron; potassium carbonate; ammonium chloride; benzotriazol-1-ol; caesium carbonate; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; copper(I) bromide; sodium hydroxide; trichlorophosphate;
In
tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile;