Multi-step reaction with 10 steps
1.1: n-butyllithium / tetrahydrofuran; hexane / 2.5 h / -78 - -60 °C / Inert atmosphere
1.2: 1 h / -60 - 20 °C / Inert atmosphere
2.1: N-Bromosuccinimide / tetrahydrofuran / 24 h / 20 °C
3.1: caesium carbonate / tetrahydrofuran / 0.33 h / 20 °C
3.2: 20 °C
4.1: sodium tetrahydroborate / ethanol / 1 h / 20 °C / Inert atmosphere
5.1: phosphorus tribromide / 1,4-dioxane / 2 h / 40 °C / Inert atmosphere
6.1: toluene / 120 °C / Inert atmosphere
7.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 0.75 h / Inert atmosphere
7.2: 20 °C / Inert atmosphere
8.1: potassium carbonate; [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(ll) dichloride / water; isopropyl alcohol / 0.5 h / 130 °C / Microwave irradiation
9.1: palladium 10% on activated carbon; ammonium formate / water; ethanol / 2 h / 90 °C / Inert atmosphere
10.1: hydrogenchloride / 1,4-dioxane / 5 h / Inert atmosphere
With
hydrogenchloride; sodium tetrahydroborate; N-Bromosuccinimide; n-butyllithium; [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(ll) dichloride; palladium 10% on activated carbon; ammonium formate; phosphorus tribromide; potassium carbonate; caesium carbonate; lithium diisopropyl amide;
In
tetrahydrofuran; 1,4-dioxane; ethanol; hexane; water; isopropyl alcohol; toluene;