Multi-step reaction with 10 steps
1.1: pyridine / dmap / 50 °C / Inert atmosphere
1.2: 5 h / 50 °C
2.1: pyridinium chlorochromate / dichloromethane / 7.25 h / 20 °C / Inert atmosphere
3.1: potassium hexamethylsilazane / tetrahydrofuran / 0.25 h / -78 °C / Inert atmosphere
3.2: 4.5 h / -78 °C
4.1: sodium carbonate monohydrate / tetrakis(triphenylphosphine) palladium(0) / isopropyl alcohol; 1,4-dioxane; water / 3.5 h / Inert atmosphere
5.1: water; lithium hydroxide monohydrate / 1,4-dioxane / 25.5 h / 75 °C / Inert atmosphere
6.1: pyridinium chlorochromate / dichloromethane / 6.5 h / 20 °C / Inert atmosphere
7.1: potassium carbonate; hydroxylamine hydrochloride / ethanol / 2 h / 50 °C / Inert atmosphere
8.1: sodium cyanoborohydride; ammonium acetate / titanium(III) chloride / ethanol / 1 h / 20 °C / Cooling with ice; Inert atmosphere
9.1: 1,4-dioxane; methanol / 144 h / 20 °C / Inert atmosphere
10.1: 1,4-dioxane; methanol / 72 h / 20 °C / Inert atmosphere
With
pyridine; sodium carbonate monohydrate; lithium hydroxide monohydrate; hydroxylamine hydrochloride; ammonium acetate; water; potassium hexamethylsilazane; sodium cyanoborohydride; potassium carbonate; pyridinium chlorochromate;
dmap; tetrakis(triphenylphosphine) palladium(0); titanium(III) chloride;
In
tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; water; isopropyl alcohol;
4.1: Suzuki Coupling;