Multi-step reaction with 13 steps
1.1: copper(l) iodide; copper diacetate / water / 48 h / 100 °C
2.1: polyphosphoric acid / 3 h / 90 °C
3.1: triethylamine / dichloromethane / 3 h / 0 - 20 °C
4.1: n-butyllithium / tetrahydrofuran; hexane / 2 h / 0 °C
4.2: 0 - 20 °C
5.1: diethylzinc / hexane; toluene / 0 - 20 °C
6.1: N-Bromosuccinimide / dichloromethane / 1 h / 0 - 20 °C
7.1: boron tribromide / dichloromethane / 1 h / -20 - 0 °C
7.2: Cooling with ice
8.1: triethylamine / dmap / tetrahydrofuran / 10 h / 0 - 20 °C
9.1: piperidine / bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; tri-tert-butyl phosphine / N,N-dimethyl-formamide / 80 °C / Inert atmosphere
10.1: hydrogenchloride / 1,4-dioxane / 2 h / 20 °C
11.1: sodium acetate; potassium carbonate / copper dichloride; palladium dichloride / 20 °C
12.1: lithium hydroxide / tetrahydrofuran; methanol / 2 h / 70 °C
12.2: 20 °C
13.1: HATU / N,N-dimethyl-formamide / 0.5 h / 20 °C
13.2: 0.33 h / 20 °C
With
piperidine; hydrogenchloride; N-Bromosuccinimide; n-butyllithium; diethylzinc; sodium acetate; boron tribromide; potassium carbonate; triethylamine; HATU; lithium hydroxide;
dmap; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; tri-tert-butyl phosphine; copper diacetate; copper dichloride; palladium dichloride;
In
tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene;