Multi-step reaction with 17 steps
1.1: sulfuric acid; nitric acid / dichloromethane / 0 - 20 °C
2.1: sodium dithionite; water / tetrahydrofuran / 16 h / 20 °C
3.1: pyridinium hydrobromide perbromide / dichloromethane / 1 h / 0 °C
4.1: hydrogenchloride; sodium nitrite / 1,4-dioxane; water / 0.5 h / 20 °C
4.2: 72 h / 0 - 20 °C
5.1: isopropylmagnesium chloride; lithium chloride / tetrahydrofuran / 1 h / -78 °C
5.2: 2 h / -78 - 20 °C
6.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 1.5 h / 0 - 20 °C
7.1: N-ethyl-N,N-diisopropylamine / dmap / dichloromethane / 20 °C
8.1: n-butyllithium; Di-sec-butylamin; N,N,N,N,-tetramethylethylenediamine; triethylamine hydrochloride / tetrahydrofuran; hexane / 1 h / -78 °C
8.2: 2.02 h / -78 - 20 °C
9.1: boron tribromide / dichloromethane / 1 h / -78 - 0 °C
9.2: 0.25 h / 20 °C
10.1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 20 °C
11.1: n-butyllithium / tetrahydrofuran / 0.33 h / -100 °C / Inert atmosphere
11.2: 1.08 h / -100 - -78 °C
12.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C
13.1: sodium tetrahydroborate / 1,2-dichloro-ethane / 2 h / 20 °C
14.1: potassium carbonate / acetonitrile / 2 h / 30 °C
15.1: n-butyllithium; N,N,N,N,-tetramethylethylenediamine; diisopropylamine / tetrahydrofuran; hexane / 0.17 h / -78 °C
15.2: 1 h / -78 - 0 °C
16.1: 1,3-dimethylbarbituric acid / tetrakis(triphenylphosphine) palladium(0) / dichloromethane / 24 h / 35 °C / Inert atmosphere
17.1: benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / 20 °C
With
hydrogenchloride; sodium tetrahydroborate; n-butyllithium; sodium dithionite; oxalyl dichloride; 1,3-dimethylbarbituric acid; Di-sec-butylamin; N,N,N,N,-tetramethylethylenediamine; sulfuric acid; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; water; isopropylmagnesium chloride; nitric acid; boron tribromide; triethylamine hydrochloride; potassium carbonate; pyridinium hydrobromide perbromide; diisopropylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; lithium chloride; sodium nitrite;
dmap; tetrakis(triphenylphosphine) palladium(0); N,N-dimethyl-formamide;
In
tetrahydrofuran; 1,4-dioxane; hexane; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetonitrile;