Multi-step reaction with 9 steps
1.1: lithium diisopropyl amide / water; tetrahydrofuran / 1.67 h / -78 - -40 °C / Inert atmosphere
1.2: 2 h / -78 °C
2.1: 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; caesium carbonate; palladium diacetate / 1,4-dioxane / 8 h / 110 °C / Inert atmosphere
3.1: sodium hydride / water; tetrahydrofuran; N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere
3.2: 0.5 h / 20 °C
4.1: water; tetrahydrofuran / 1 h / 0 °C / Inert atmosphere
5.1: Grubbs catalyst first generation / 1,2-dichloro-ethane / 5 h / 20 °C / Reflux; Inert atmosphere
6.1: acetic acid; palladium(II) hydroxide; hydrogen / ethanol / 6 h / 20 °C / Inert atmosphere
7.1: sodium hydride / N,N-dimethyl-formamide / 0.17 h / Inert atmosphere
7.2: 20 - 90 °C
8.1: pyridinium tribromide / chloroform / 2 h / 20 °C / Inert atmosphere
9.1: ethanol; acetone / 90 °C / Inert atmosphere
With
Grubbs catalyst first generation; pyridinium tribromide; hydrogen; palladium diacetate; palladium(II) hydroxide; sodium hydride; caesium carbonate; acetic acid; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; lithium diisopropyl amide;
In
tetrahydrofuran; 1,4-dioxane; ethanol; chloroform; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetone;
2.1: |Buchwald-Hartwig Coupling;