Multi-step reaction with 10 steps
1.1: lithium hexamethyldisilazane / tetrahydrofuran / 18 h / 20 °C
2.1: hydroxylamine hydrochloride; sodium hydroxide / methanol; water / 2 h / Reflux
3.1: trifluoroacetic anhydride / 1,2-dimethoxyethane / 0.67 h / 20 °C / Inert atmosphere
3.2: 6.5 h / 0 °C / Inert atmosphere
3.3: 16 h / 70 °C / Inert atmosphere
4.1: potassium acetate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 18 h / 100 °C / Inert atmosphere; sealed tube
5.1: cesium fluoride / dichlorobis(chlorodi-tert-butylphosphine) palladium(II) / N,N-dimethyl-formamide / 18 h / 90 °C
6.1: N-iodo-succinimide / dichloromethane; acetonitrile / 2 h / 20 °C
7.1: XPhos / dichloro bis(acetonitrile) palladium(II) / 1,4-dioxane / 2 h / 110 °C / microwave tube; Inert atmosphere; sealed tube
8.1: potassium phosphate / tris-(dibenzylideneacetone)dipalladium(0) / tetrahydrofuran; water / 18 h / 90 °C / Inert atmosphere; microwave tube; sealed tube
9.1: lithium hydroxide monohydrate / tetrahydrofuran; water / 24 h / 20 °C
9.2: pH 6
10.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 18 h / 20 °C
With
potassium phosphate; N-iodo-succinimide; lithium hydroxide monohydrate; hydroxylamine hydrochloride; potassium acetate; N-ethyl-N,N-diisopropylamine; cesium fluoride; HATU; trifluoroacetic anhydride; sodium hydroxide; lithium hexamethyldisilazane; XPhos;
dichloro bis(acetonitrile) palladium(II); tris-(dibenzylideneacetone)dipalladium(0); dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; dichlorobis(chlorodi-tert-butylphosphine) palladium(II);
In
tetrahydrofuran; 1,4-dioxane; methanol; 1,2-dimethoxyethane; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;