Multi-step reaction with 7 steps
1.1: cesium fluoride / 1,2-dimethoxyethane / 1 h / 20 °C / Inert atmosphere; Sonication
1.2: 1 h / 20 °C / Inert atmosphere
2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 20 °C / Inert atmosphere; Sonication
2.2: 1.5 h / 50 °C / Inert atmosphere
3.1: palladium 10% on activated carbon; hydrogen / ethanol / 1.5 h / 50 °C / 2844.39 Torr / Inert atmosphere
4.1: bromine; acetic acid / 1,4-dioxane / 1 h / 20 °C / Inert atmosphere
5.1: bromine; acetic acid / 2 h / 100 °C / Inert atmosphere
6.1: caesium carbonate / water; 1,4-dioxane / 0.17 h / Inert atmosphere
6.2: 2 h / 50 °C / Inert atmosphere
7.1: tris(dibenzylideneacetone)dipalladium(0) chloroform complex; tert-butyl XPhos; sodium t-butanolate / toluene / 1.5 h / 20 °C / Inert atmosphere
With
tris(dibenzylideneacetone)dipalladium(0) chloroform complex; palladium 10% on activated carbon; hydrogen; bromine; sodium hydride; caesium carbonate; acetic acid; cesium fluoride; sodium t-butanolate; tert-butyl XPhos;
In
tetrahydrofuran; 1,4-dioxane; 1,2-dimethoxyethane; ethanol; water; toluene; mineral oil;
DOI:10.1021/jm401329s