Multi-step reaction with 13 steps
1: C28H27F6N3O3S / tetrahydrofuran / 24 h / -20 °C
2: diphenylphosphoranyl azide; triethylamine / toluene / 15 h / 90 °C
3: trifluoroacetic acid / dichloromethane / 1 h / 20 °C
4: triethylamine / dichloromethane / 1 h / 20 °C
5: tetrakis(triphenylphosphine) palladium(0); morpholine / tetrahydrofuran / 1 h / 20 °C
6: dichloromethane / 2 h / 20 °C
7: N-chloro-succinimide / dichloromethane / 2 h / 20 °C
8: 18 h / 60 °C
9: hydrogenchloride / dichloromethane; water / 4 h / 40 °C
10: thionyl chloride / 1 h / 20 °C
11: acetic acid / toluene / 2 h / 110 °C
12: sodium cyanoborohydride / 6 h / 20 °C
13: triethylamine / dichloromethane / 5 h / 0 - 40 °C
With
morpholine; hydrogenchloride; N-chloro-succinimide; tetrakis(triphenylphosphine) palladium(0); thionyl chloride; C28H27F6N3O3S; diphenylphosphoranyl azide; sodium cyanoborohydride; acetic acid; triethylamine; trifluoroacetic acid;
In
tetrahydrofuran; dichloromethane; water; toluene;
2: |Curtius Rearrangement;
DOI:10.1016/j.bmcl.2012.09.103