Multi-step reaction with 8 steps
1.1: hydrazine / methanol / 24 h / 20 °C
2.1: sodium nitrite; acetic acid / water; methanol / 0 °C
2.2: 24 h / Heating; Reflux
3.1: sodiumsulfide nonahydrate / ethanol; water / 18 h / 20 °C
4.1: pyridine; sodium nitrite; hydrogen fluoride / water / 0 - 80 °C / Ice/salt bath; Sealed tube
5.1: water; iron / 2 h / 100 °C
6.1: potassium carbonate / tetrakis(triphenylphosphine) palladium(0); XPhos / 1,4-dioxane / 18 h / Heating; Reflux; Inert atmosphere
7.1: hydrogen bromide; acetic acid / 12 h / 80 °C
7.2: pH 8
8.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 36 h / 20 °C / Inert atmosphere
With
pyridine; sodiumsulfide nonahydrate; hydrogen fluoride; water; hydrogen bromide; iron; potassium carbonate; acetic acid; N-ethyl-N,N-diisopropylamine; HATU; hydrazine; sodium nitrite;
tetrakis(triphenylphosphine) palladium(0); XPhos;
In
1,4-dioxane; methanol; ethanol; water; N,N-dimethyl-formamide;