Multi-step reaction with 17 steps
1.1: tetra-N-butylammonium tribromide / 18 h / 20 °C
2.1: 1H-imidazole / dichloromethane / 15 h / 0 - 20 °C
3.1: lithium diisopropyl amide / tetrahydrofuran / 1 h / -78 °C
3.2: 1 h / -78 - 0 °C
4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 0 °C
5.1: hydrogenchloride / water; acetone / 1 h / Reflux
6.1: nitric acid / chloroform / 4 h / 20 °C
7.1: ammonium chloride; iron / water; tetrahydrofuran; methanol / 3 h / Reflux
8.1: pyridine / dichloromethane / 15 h / 0 - 20 °C
9.1: potassium carbonate; potassium iodide / N,N-dimethyl-formamide / 15 h / Inert atmosphere; Reflux
10.1: water; lithium hydroxide monohydrate / 1,4-dioxane / 3 h / Reflux
10.2: pH 3
11.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0.5 h / 20 °C
11.2: 15 h
12.1: potassium phosphate / [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) / N,N-dimethyl-formamide / 15 h / 90 °C / Inert atmosphere
13.1: hydrogen / palladium on activated charcoal / methanol / 24 h / 25 °C / 2068.65 Torr
14.1: iodine; isopentyl nitrite / copper(l) iodide / acetonitrile / 7 h / 25 - 90 °C
15.1: potassium phosphate / [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) / N,N-dimethyl-formamide / 15 h / 90 °C / Inert atmosphere
16.1: dihydrogen peroxide / acetic acid / 3 h / 65 °C
17.1: hydrogen / palladium on activated charcoal / methanol / 24 h / 20 °C / 2068.65 Torr
With
pyridine; 1H-imidazole; hydrogenchloride; potassium phosphate; lithium hydroxide monohydrate; tetrabutyl ammonium fluoride; water; hydrogen; dihydrogen peroxide; iodine; nitric acid; tetra-N-butylammonium tribromide; iron; potassium carbonate; ammonium chloride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; potassium iodide; lithium diisopropyl amide; isopentyl nitrite;
copper(l) iodide; [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); palladium on activated charcoal;
In
tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; chloroform; water; acetic acid; N,N-dimethyl-formamide; acetone; acetonitrile;