Multi-step reaction with 9 steps
1.1: magnesium sulfate / dichloromethane / 20 °C
2.1: magnesium sulfate / dichloromethane / 20 °C
3.1: sodium tetrahydroborate / tetrahydrofuran; methanol / 48 h / 20 °C
4.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / 20 °C
5.1: sodium carbonate; triphenylphosphine / palladium diacetate / propan-1-ol; water; N,N-dimethyl-formamide / 18 h / 90 °C / Inert atmosphere of nitrogen
6.1: 1,4-di(diphenylphosphino)-butane; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane / bis(1,5-cyclooctadiene)diiridium(I) dichloride / tetrahydrofuran / 12 h / 20 °C
6.2: 12 h / 20 °C
7.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 0 - 20 °C
8.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride / tetrahydrofuran / 0.25 h / 20 °C
9.1: hydrogen / palladium 10% on activated carbon / ethyl acetate / 1.5 h
With
sodium tetrahydroborate; hydrogen; sodium hydrogencarbonate; sodium carbonate; magnesium sulfate; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; triphenylphosphine; 1,4-di(diphenylphosphino)-butane; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane; lithium chloride;
bis(1,5-cyclooctadiene)diiridium(I) dichloride; palladium 10% on activated carbon; palladium diacetate;
In
tetrahydrofuran; methanol; propan-1-ol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide;
5.1: Suzuki Coupling;