Multi-step reaction with 10 steps
1.1: tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide / acetonitrile / 0.5 h / 20 °C / Inert atmosphere
1.2: 30 - 40 °C
2.1: lithium diisopropyl amide / hexane; tetrahydrofuran / 1.83 h / -78 °C / Inert atmosphere
2.2: 4 h / -78 °C
3.1: caesium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,2-dimethoxyethane; water / 14 h / 95 °C / Nitrogen
4.1: N-iodo-succinimide / tetrahydrofuran; methanol / 1 h
5.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,2-dimethoxyethane / Nitrogen
6.1: hydrogenchloride / ethanol; water / 2.5 h / 60 °C
6.2: pH 8
7.1: 1,1-dichloroethane; water / 3.5 h
8.1: bromo-catecholborane / dichloromethane / 1.5 h
9.1: caesium carbonate / 1,2-dimethoxyethane; DMPU 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / 17 h / 50 °C
10.1: lithium triethylborohydride / tetrahydrofuran / 4 h
With
hydrogenchloride; N-iodo-succinimide; bromo-catecholborane; tetra(n-butyl)ammonium hydrogensulfate; lithium triethylborohydride; caesium carbonate; sodium hydroxide; lithium diisopropyl amide;
dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2;
In
tetrahydrofuran; methanol; 1,2-dimethoxyethane; 1,1-dichloroethane; ethanol; hexane; dichloromethane; DMPU 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; water; acetonitrile;
5.1: Suzuki Coupling;