Multi-step reaction with 12 steps
1.1: diisopropylamine; n-butyllithium / hexane; tetrahydrofuran / 1 h / -78 °C
1.2: 1 h
2.1: diethyl ether / 12 h / 20 °C / Cooling with ice
2.2: 0 °C
3.1: dipyridinium dichromate / N,N-dimethyl-formamide / 12 h / 20 °C
4.1: aluminum (III) chloride / dichloromethane / 12 h / 20 °C / Cooling with ice
5.1: pyridine / dichloromethane / 3 h / 45 °C / Cooling with ice
6.1: sodium hydride / dimethyl sulfoxide / 0 - 20 °C
6.3: 12 h / Reflux
7.1: N-Bromosuccinimide / N,N-dimethyl-formamide / 12 h / 20 °C
8.1: potassium carbonate / tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane; water / 12 h / Reflux; Inert atmosphere
9.1: 2,2'-azobis(isobutyronitrile); N-Bromosuccinimide / tetrachloromethane / 12 h / 80 °C
10.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 20 °C
10.2: 12 h
11.1: hydrazine hydrate / methanol / 3 h / Reflux
12.1: N-ethyl-N,N-diisopropylamine / tert-butyl alcohol / 248 h / Reflux
With
pyridine; aluminum (III) chloride; N-Bromosuccinimide; dipyridinium dichromate; n-butyllithium; 2,2'-azobis(isobutyronitrile); sodium hydride; potassium carbonate; hydrazine hydrate; diisopropylamine; N-ethyl-N,N-diisopropylamine;
tetrakis(triphenylphosphine) palladium(0);
In
tetrahydrofuran; 1,4-dioxane; methanol; tetrachloromethane; diethyl ether; hexane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; tert-butyl alcohol;