Multi-step reaction with 9 steps
1.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 - -30 °C / Inert atmosphere
1.2: -78 - 20 °C / Inert atmosphere
2.1: diisobutylaluminium hydride / dichloromethane / 0.42 h / -78 °C / Inert atmosphere
3.1: diisopropylamine / diethyl ether; tetrahydrofuran; hexane / 0.33 h / -78 - -50 °C / Inert atmosphere
3.2: -78 - 20 °C / Inert atmosphere
4.1: n-butyllithium / tetrahydrofuran; hexane / 0.25 h / -78 °C / Inert atmosphere
4.2: -78 - 20 °C / Inert atmosphere
5.1: hydrogenchloride / tetrahydrofuran; water / 0.25 h / 20 °C
6.1: dimethyl sulfoxide; oxalyl dichloride; N-ethyl-N,N-diisopropylamine / dichloromethane / -78 - 20 °C / Inert atmosphere
7.1: triphenylphosphine; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.17 h / 0 °C / Inert atmosphere
8.1: tetrakis(triphenylphosphine) palladium(0); thallium (I) ethoxide / tetrahydrofuran; water / 20 °C / Inert atmosphere
9.1: bis(tri-t-butylphosphine)palladium(0) / toluene; tetrahydrofuran / 4.5 h / 0 °C / Inert atmosphere
With
hydrogenchloride; tetrakis(triphenylphosphine) palladium(0); n-butyllithium; oxalyl dichloride; bis(tri-t-butylphosphine)palladium(0); thallium (I) ethoxide; diisobutylaluminium hydride; dimethyl sulfoxide; diisopropylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine;
In
tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; toluene;
8.1: |Suzuki Coupling / 9.1: |Negishi Coupling;