Multi-step reaction with 8 steps
1.1: thioacetamide / methanol / 0 - 45 °C
1.2: 0 - 80 °C
2.1: iodine; sodium carbonate / 1,4-dioxane; water / 20 °C
3.1: sodium hydride / N,N-dimethyl-formamide / 20 °C
3.2: 100 °C
4.1: ethylmagnesium bromide / tetrahydrofuran; diethyl ether / -40 °C
5.1: hydrogenchloride / 1,4-dioxane; dichloromethane / 0 - 20 °C
6.1: N-ethyl-N,N-diisopropylamine / ethanol / 0.17 h / 140 °C / 4500.45 Torr / Microwave irradiation
7.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C
8.1: copper(l) iodide; N,N,N,N,N,N-hexamethylphosphoric triamide / N,N-dimethyl-formamide / 80 °C
With
hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; copper(l) iodide; ethylmagnesium bromide; iodine; sodium hydride; sodium carbonate; thioacetamide; N-ethyl-N,N-diisopropylamine;
In
tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; ethanol; dichloromethane; water; N,N-dimethyl-formamide;
6.1: |Pictet-Spengler Synthesis;
DOI:10.1016/j.bmcl.2013.01.088