Multi-step reaction with 9 steps
1.1: sodium hydride / N,N-dimethyl-formamide / 10.5 h / 0 - 20 °C
2.1: sulfuric acid; water / 1,4-dioxane / 3 h / 20 °C / Heating / reflux
3.1: dipyridinium dichromate / dichloromethane / 12 h / 0 - 20 °C / Molecular sieve
4.1: hydrogen / palladium 10% on activated carbon; palladium(II) hydroxide/carbon / methanol; water / 12 h / 20 °C / 7355.72 Torr
5.1: tetrabutylammomium bromide; di(n-butyl)tin oxide / toluene / 90 °C / Heating / reflux
6.1: pyridine / dichloromethane / 0.5 h / 0 °C
7.1: sodium azide / N,N-dimethyl-formamide / 1 h / 0 °C
8.1: 2-hydroxypyridin; N-ethyl-N,N-diisopropylamine / dichloromethane / 70 °C
8.2: 20 °C
9.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 2.42 h / 0 - 20 °C
With
pyridine; 2-hydroxypyridin; dipyridinium dichromate; sodium azide; sulfuric acid; tetrabutylammomium bromide; water; hydrogen; sodium hydride; di(n-butyl)tin oxide; N-ethyl-N,N-diisopropylamine; HATU;
palladium(II) hydroxide/carbon; palladium 10% on activated carbon;
In
1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;