Multi-step reaction with 10 steps
1: potassium carbonate / dimethyl sulfoxide / 20 °C
2: 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 3 h / 20 °C / Inert atmosphere
3: 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 8 h / 0 °C
4: trifluoromethylsulfonic anhydride; Triphenylphosphine oxide / dichloromethane / 0.5 h / 0 °C / Inert atmosphere
5: ammonium acetate; zinc / tetrahydrofuran; water / 0.5 h / 20 °C
6: tetrakis(triphenylphosphine) palladium(0); N-methylaniline / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere; Darkness
7: N-ethyl-N,N-diisopropylamine; HATU / dichloromethane / 10 h / 20 °C
8: tetrakis(triphenylphosphine) palladium(0); N-methylaniline / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere; Darkness
9: diethylamine / acetonitrile
10: N-ethyl-N,N-diisopropylamine; HATU / dichloromethane / 20.5 h / 0 - 20 °C
With
2,6-dimethylpyridine; tetrakis(triphenylphosphine) palladium(0); 1-hydroxy-7-aza-benzotriazole; trifluoromethylsulfonic anhydride; trimethylsilyl trifluoromethanesulfonate; ammonium acetate; potassium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; diethylamine; N-ethyl-N,N-diisopropylamine; HATU; N-methylaniline; Triphenylphosphine oxide; zinc;
In
tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; acetonitrile;
DOI:10.1021/ml200176m