Multi-step reaction with 11 steps
1.1: triethylsilane / dichloromethane / 2 h / 20 °C / Inert atmosphere
2.1: N-ethyl-N,N-diisopropylamine / isopropyl alcohol / 5 h / 20 °C / Inert atmosphere
3.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 0.5 h / -78 °C / Inert atmosphere
3.2: 3 h / -40 °C / Inert atmosphere
4.1: trimethylphosphane / tetrahydrofuran; toluene / 6 h / -20 - 20 °C / Inert atmosphere
5.1: lithium hydroxide monohydrate / tetrahydrofuran; water / 1 h / 0 °C / Inert atmosphere
6.1: 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere
6.2: 0 - 20 °C / Inert atmosphere
7.1: dichloromethane / 2 h / 20 °C / Inert atmosphere
8.1: 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere
8.2: 0 - 20 °C / Inert atmosphere
9.1: palladium 10% on activated carbon; hydrogen / tetrahydrofuran; water / 20 °C / 750.08 Torr / Inert atmosphere
10.1: 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 1 h / 0 °C / Inert atmosphere
11.1: methyl-phenyl-thioether; ethane-1,2-dithiol; methoxybenzene / Inert atmosphere
With
triethylsilane; 1-hydroxy-7-aza-benzotriazole; lithium hydroxide monohydrate; methyl-phenyl-thioether; palladium 10% on activated carbon; hydrogen; potassium hexamethylsilazane; ethane-1,2-dithiol; methoxybenzene; N-ethyl-N,N-diisopropylamine; HATU; trimethylphosphane;
In
tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; isopropyl alcohol; toluene;
DOI:10.1002/chem.201200457