Multi-step reaction with 10 steps
1.1: copper(II) sulfate; sodium hydroxide / water / 0.17 h / 60 °C / Inert atmosphere
1.2: 12 h / 20 °C / Inert atmosphere
1.3: Inert atmosphere
2.1: thionyl chloride / 2 h / 20 °C / Inert atmosphere; Cooling
3.1: benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine / dichloromethane / 3 h / 20 °C / Inert atmosphere
4.1: hydrogenchloride / 1,4-dioxane / 5 h / 20 °C / Inert atmosphere
5.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 1 h / 0 °C / Inert atmosphere
5.2: 16 h / 0 - 20 °C / Inert atmosphere
6.1: hydrogenchloride / 1,4-dioxane / 5 h / 20 °C / Inert atmosphere
7.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 1 h / 0 °C / Inert atmosphere
7.2: 16 h / 0 - 20 °C / Inert atmosphere
8.1: hydrogenchloride / 1,4-dioxane / 5 h / 20 °C / Inert atmosphere
9.1: benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 12 h / 20 °C / Inert atmosphere
10.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; cesium fluoride / 1,4-dioxane; water / 18 h / 90 °C / Inert atmosphere
With
hydrogenchloride; thionyl chloride; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; benzotriazol-1-ol; copper(II) sulfate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; cesium fluoride; sodium hydroxide;
In
1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide;
10.1: Suzuki-Miyaura cyclization;
DOI:10.1021/jo202105v