Multi-step reaction with 7 steps
1.1: magnesium; iodine / ethylene dibromide; tetrahydrofuran / 3 h / Reflux; Inert atmosphere
1.2: 2.5 h / -78 - 0 °C / Inert atmosphere
2.1: n-butyllithium; 1,1,1,3,3,3-hexamethyl-disilazane; lithium hexamethyldisilazane / hexane; tetrahydrofuran / 1 h / -78 - 0 °C / Inert atmosphere
2.2: 3.5 h / -78 - -30 °C / Inert atmosphere
3.1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane / 3 h / 50 °C / Inert atmosphere
4.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 2 h / 0 - 20 °C / pH 7 / Inert atmosphere
5.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 0.75 h / 0 - 20 °C / Inert atmosphere
6.1: calcium hydride; dicyclohexylboron chloride; triethylamine / benzene; diethyl ether / 1.08 h / -78 - 0 °C / Inert atmosphere
6.2: 17.5 h / -78 - -20 °C / Inert atmosphere
7.1: 1H-imidazole / dichloromethane / 0.5 h / 0 - 20 °C / Inert atmosphere
With
1H-imidazole; tetrakis(triphenylphosphine) palladium(0); n-butyllithium; calcium hydride; dicyclohexylboron chloride; iodine; sodium hydrogencarbonate; potassium carbonate; Dess-Martin periodane; magnesium; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium hexamethyldisilazane;
In
tetrahydrofuran; 1,4-dioxane; diethyl ether; hexane; dichloromethane; ethylene dibromide; benzene;
3.1: |Suzuki Coupling;
DOI:10.1002/anie.201310164