Multi-step reaction with 10 steps
1.1: hydroxylamine hydrochloride; sodium sulfate
2.1: sulfuric acid / 0.5 h / 60 °C
3.1: hydroxylamine hydrochloride / water; ethanol / 12 h
4.1: 2,6-dimethylpyridine; trifluoromethylsulfonic anhydride / dichloromethane / 3 h / 0 °C / Cooling with ice; Reflux
4.2: 1 h / 20 - 30 °C
5.1: borane-THF / tetrahydrofuran / 72 h / 0 - 20 °C / Inert atmosphere
6.1: tetrahydrofuran / 6 h / 20 - 80 °C
7.1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide / 14 h / 80 °C / Inert atmosphere
8.1: hydrogen; palladium 10% on activated carbon / tetrahydrofuran / 12 h
9.1: dichloromethane; tetrahydrofuran / 6 h / 0 - 20 °C
10.1: triethylamine / dimethyl sulfoxide / 0.5 h / 0 - 20 °C
10.2: 6 h
With
2,6-dimethylpyridine; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; borane-THF; trifluoromethylsulfonic anhydride; sulfuric acid; palladium 10% on activated carbon; hydroxylamine hydrochloride; hydrogen; potassium acetate; sodium sulfate; triethylamine;
In
tetrahydrofuran; ethanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide;
7.1: |Suzuki-Miyaura Coupling;
DOI:10.2174/15734064113096660046