Multi-step reaction with 10 steps
1.1: aluminum (III) chloride / dichloromethane / 0 - 20 °C
2.1: triethylsilane; boron trifluoride diethyl etherate / chloroform; acetonitrile / 0 - 20 °C
3.1: n-butyllithium / toluene; hexane; tetrahydrofuran / 0.42 h / -78 °C / Inert atmosphere
3.2: 1.33 h / -78 °C / Inert atmosphere
4.1: methanesulfonic acid / toluene; hexane; tetrahydrofuran / -78 - 20 °C / Inert atmosphere
5.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 2 h / -78 - 0 °C / Inert atmosphere
6.1: pyridine; dmap / chloroform / 1 h / 20 °C
7.1: palladium 10% on activated carbon; triethylamine; hydrogen / methanol; tetrahydrofuran / 18 h / 20 °C
8.1: pyridine; bromine / chloroform / 0.17 h / 0 - 20 °C
9.1: copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane / 2 h / Inert atmosphere; Reflux
10.1: sodium methylate / methanol; tetrahydrofuran / 1 h / 20 °C
With
pyridine; triethylsilane; dmap; aluminum (III) chloride; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); n-butyllithium; methanesulfonic acid; palladium 10% on activated carbon; boron trifluoride diethyl etherate; hydrogen; bromine; sodium methylate; triethylamine;
In
tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; chloroform; toluene; acetonitrile;
3.2: |Barbier Coupling Reaction;
DOI:10.1016/j.bmc.2013.05.048