Multi-step reaction with 6 steps
1.1: pyridine / dichloromethane / 0.5 h / 0 °C / Molecular sieve
1.2: 16 h / 0 - 20 °C / Molecular sieve
2.1: 4-nitro-4-methyl-2,3,5,6-tetrabromo-2,5-cyclohexadien-1-one / tetrahydrofuran; diethyl ether / 5 h / 20 °C
3.1: hydrogen; palladium 10% on activated carbon; acetic acid / methanol / 24 h / 3102.97 Torr
4.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / N,N-dimethyl-formamide / 0.5 h / 0 °C / Molecular sieve; Inert atmosphere
4.2: 24 h / 20 °C / Inert atmosphere; Molecular sieve
5.1: potassium carbonate / methanol; water / 2 h / Inert atmosphere; Reflux
6.1: potassium carbonate; potassium iodide / N,N-dimethyl-formamide / 20 °C
With
pyridine; palladium 10% on activated carbon; 4-nitro-4-methyl-2,3,5,6-tetrabromo-2,5-cyclohexadien-1-one; hydrogen; potassium carbonate; benzotriazol-1-ol; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; potassium iodide;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/j.bmcl.2014.03.073