Multi-step reaction with 13 steps
1.1: methanol / 50 °C / Inert atmosphere
2.1: sodium hydrogencarbonate / 1,4-dioxane / 20 °C / Inert atmosphere
3.1: N-ethyl-N,N-diisopropylamine; sodium iodide / 1,2-dimethoxyethane / 0 - 20 °C / Inert atmosphere
4.1: sodium / toluene; methanol / 48 h / 20 °C / Inert atmosphere
5.1: sodium hydride / tetrahydrofuran / 0.33 h / 0 °C / Inert atmosphere
5.2: 20 °C
6.1: sodium hydrogencarbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane; water / 0.33 h / 150 °C / Inert atmosphere; Microwave irradiation
7.1: sodium iodide; sodium hydride / N,N-dimethyl-formamide / 0.33 h / 20 °C / Inert atmosphere
7.2: 2.5 h / 55 °C / Inert atmosphere
8.1: hydrogenchloride / water; methanol / 1 h / 55 °C / Inert atmosphere
9.1: sodium hydrogencarbonate / 1,4-dioxane; water / 20 °C / Inert atmosphere
10.1: triethylamine / dichloromethane / 4 h / 0 °C / Inert atmosphere
11.1: sodium azide / N,N-dimethyl-formamide / 5 h / 80 °C / Inert atmosphere
12.1: triphenylphosphine / water; tetrahydrofuran / 3 h / Inert atmosphere; Reflux
13.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C / Inert atmosphere
With
hydrogenchloride; sodium azide; sodium; sodium hydride; sodium hydrogencarbonate; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; trifluoroacetic acid; sodium iodide;
(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride;
In
tetrahydrofuran; 1,4-dioxane; methanol; 1,2-dimethoxyethane; dichloromethane; water; N,N-dimethyl-formamide; toluene;