Multi-step reaction with 8 steps
1: palladium 10% on activated carbon; camphor-10-sulfonic acid; hydrogen / methanol / 12 h / 20 °C
2: pyridine / 3 h / 20 °C / Inert atmosphere
3: N,N,N',N'-tetramethyl-1,8-diaminonaphthalene / dichloromethane / 2 h / 20 °C / Inert atmosphere
4: acetic acid; zinc / 6 h / 20 °C / Inert atmosphere
5: potassium carbonate / N,N-dimethyl-formamide / 0.67 h / 20 °C / Inert atmosphere
6: hydrogenchloride; water / methanol / 8 h / 60 °C / Inert atmosphere
7: triethylamine / tetrahydrofuran / 0 °C / Inert atmosphere
8: 1-thiopropane; potassium tert-butylate / N,N-dimethyl-formamide / 150 °C
With
pyridine; hydrogenchloride; 1-thiopropane; palladium 10% on activated carbon; camphor-10-sulfonic acid; potassium tert-butylate; water; hydrogen; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; potassium carbonate; acetic acid; triethylamine; zinc;
In
tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/j.bmc.2010.12.035