Multi-step reaction with 7 steps
1.1: potassium acetate / tris-(dibenzylideneacetone)dipalladium(0); XPhos / 1,4-dioxane / 110 °C / Inert atmosphere
2.1: potassium phosphate / tris-(dibenzylideneacetone)dipalladium(0); dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane / butan-1-ol; water / 100 °C / Inert atmosphere
3.1: hydrogen / palladium 10% on activated carbon / dichloromethane; ethanol / 20 °C
4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C
5.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 2.5 h / 20 °C
6.1: lithium diisopropyl amide / hexane; pentane; tetrahydrofuran; ethylbenzene / 0.5 h / -78 - 20 °C
6.2: -78 - 20 °C
7.1: trimethylsilyl bromide / dichloromethane / 2 h / 0 - 20 °C
With
potassium phosphate; trimethylsilyl bromide; tetrabutyl ammonium fluoride; hydrogen; potassium acetate; lithium diisopropyl amide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione;
dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium(0); palladium 10% on activated carbon; XPhos;
In
tetrahydrofuran; 1,4-dioxane; ethanol; hexane; dichloromethane; ethylbenzene; water; dimethyl sulfoxide; pentane; butan-1-ol;