Multi-step reaction with 11 steps
1.1: hydrogenchloride / ethanol; water / 0.33 h / Reflux
2.1: tetrahydrofuran; diethyl ether / 0 °C / Reflux
2.2: pH 7
3.1: toluene-4-sulfonic acid; potassium iodide; sodium nitrite / water; acetonitrile / 0 - 20 °C
3.2: pH 9 - 10
4.1: tert-Butoxybis(dimethylamino)methane / 114 - 120 °C / Inert atmosphere
5.1: lithium hydroxide / iso-butanol / 20 h / 110 °C
6.1: trifluoroacetic acid; sodium nitrite / 0 - 20 °C
7.1: trichlorophosphate / 16 h / 110 °C
8.1: triethylamine / 1,4-dioxane; isopropyl alcohol / 48 h / 125 °C
9.1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / ethanol; water; toluene / 16 h / 80 °C
10.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C
11.1: triethylamine / 2-methyltetrahydrofuran / -5 - 20 °C
11.2: pH 6 - 6.5
11.3: 0.17 h / 20 °C / pH 7 - 7.5
With
hydrogenchloride; tert-Butoxybis(dimethylamino)methane; sodium carbonate; toluene-4-sulfonic acid; triethylamine; trifluoroacetic acid; potassium iodide; lithium hydroxide; sodium nitrite; trichlorophosphate;
tetrakis(triphenylphosphine) palladium(0);
In
tetrahydrofuran; 2-methyltetrahydrofuran; 1,4-dioxane; diethyl ether; ethanol; dichloromethane; water; isopropyl alcohol; toluene; acetonitrile; iso-butanol;