Multi-step reaction with 11 steps
1: N-ethyl-N,N-diisopropylamine; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / tetrahydrofuran / 3 h / 0 °C
2: Dess-Martin periodane / dichloromethane / 6 h / 20 °C / Inert atmosphere
3: triethylamine; triphenylphosphine; iodine / dichloromethane / 15 h / 0 - 20 °C
4: tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane / 48 h / 80 °C
5: hydrogen bromide; acetic acid / 28 h / 20 °C
6: triethylamine / dichloromethane / 4 h / 0 °C
7: 2,6-dimethylpyridine; dmap / dichloromethane / 2 h / 0 °C
8: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 1 h / 45 °C
9: palladium; hydrogen / dichloromethane; ethanol / 3.5 h / 20 °C / 750.08 Torr
10: N-ethyl-N,N-diisopropylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 18 h / 0 - 20 °C
11: hydrogenchloride / 1,4-dioxane / 6.5 h / 20 °C
With
2,6-dimethylpyridine; hydrogenchloride; dmap; tetrakis(triphenylphosphine) palladium(0); benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; hydrogen bromide; hydrogen; iodine; benzotriazol-1-ol; Dess-Martin periodane; palladium; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine;
In
tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; N,N-dimethyl acetamide; N,N-dimethyl-formamide;
2: |Dess-Martin Oxidation / 4: |Stille Cross Coupling / 8: |Negishi Coupling;
DOI:10.1002/anie.201302372