Multi-step reaction with 7 steps
1.1: magnesium; iodine / tetrahydrofuran / 6.17 h / Sealed tube; Inert atmosphere; Reflux
1.2: 20 °C / Sealed tube; Inert atmosphere
2.1: trifluoroacetic acid; triethylsilane; sodium hydrogencarbonate / dichloromethane / 1 h / 20 °C / Inert atmosphere
3.1: boron tribromide / dichloromethane / 20 °C
4.1: tetra-n-butylammonium tribromide / chloroform / 20 °C
5.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / 2 h / 80 °C / Inert atmosphere
5.2: 80 °C / Inert atmosphere
6.1: sodium carbonate; tris-(o-tolyl)phosphine; dichlorobis(tri-O-tolylphosphine)palladium / dichloromethane; water / 0.5 h / 80 °C / Inert atmosphere; Sealed tube
6.2: 20 - 80 °C / Inert atmosphere; Sealed tube
7.1: potassium carbonate / acetone / 1 h / Inert atmosphere; Sealed tube; Reflux
7.2: Inert atmosphere; Sealed tube; Reflux
With
triethylsilane; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; dichlorobis(tri-O-tolylphosphine)palladium; tetra-n-butylammonium tribromide; iodine; potassium acetate; boron tribromide; sodium hydrogencarbonate; sodium carbonate; potassium carbonate; magnesium; tris-(o-tolyl)phosphine; trifluoroacetic acid;
In
tetrahydrofuran; 1,4-dioxane; dichloromethane; chloroform; water; acetone;
5.1: |Miyaura Borylation Reaction / 6.1: |Suzuki Coupling;
DOI:10.1016/j.bmc.2013.10.051