Multi-step reaction with 13 steps
1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C / Inert atmosphere
1.2: 12 h / -78 - 20 °C / Inert atmosphere
2.1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran; water / 3 h / 66 °C / Inert atmosphere
3.1: toluene-4-sulfonic acid hydrazide / 1,4-dioxane / 0.33 h / 80 °C
3.2: 1.33 h / 90 °C
4.1: caesium carbonate; 1,10-Phenanthroline; copper(l) iodide / N,N-dimethyl-formamide / 1.67 h / 80 °C / Inert atmosphere
5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0 - 20 °C
6.1: 5%-palladium/activated carbon; hydrogen / ethyl acetate / 4.75 h / 760.05 Torr
7.1: benzenesulfonyl chloride; N-ethyl-N,N-diisopropylamine / ethyl acetate / 0 - 20 °C
8.1: silver carbonate / 1,4-dioxane / 41 h / 50 - 55 °C / Inert atmosphere
9.1: sodium tetrahydroborate / tetrahydrofuran; water / 1.5 h / 20 °C
10.1: triethylamine / dichloromethane / 3 h / 0 - 20 °C
11.1: dimethyl sulfoxide / 5.8 h / 60 °C
12.1: hydrogenchloride / dichloromethane; acetic acid methyl ester / 25 h / 20 - 35 °C
13.1: water; lithium hydroxide / tetrahydrofuran / 3.5 h / 20 °C
With
hydrogenchloride; sodium tetrahydroborate; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); 1,10-Phenanthroline; oxalyl dichloride; 5%-palladium/activated carbon; water; hydrogen; potassium carbonate; caesium carbonate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; benzenesulfonyl chloride; toluene-4-sulfonic acid hydrazide; silver carbonate; lithium hydroxide;
In
tetrahydrofuran; 1,4-dioxane; dichloromethane; acetic acid methyl ester; water; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide;