Multi-step reaction with 12 steps
1.1: 1.5 h / 0 - 20 °C
2.1: potassium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / toluene; ethanol; water / 2.5 h / 50 °C / Inert atmosphere; Sealed tube
3.1: Pyridine hydrobromide / dichloromethane / 0.5 h / Cooling with ice
4.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 1.5 h / Inert atmosphere; Reflux
5.1: boron tribromide / dichloromethane / 3.5 h / -78 - 20 °C
6.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dmap / dichloromethane / 20 °C
7.1: n-butyllithium / hexane; tetrahydrofuran / 0.5 h / -78 °C
7.2: -78 - 20 °C
8.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.25 h / 0 °C
9.1: (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / toluene / 3 h / -20 °C
10.1: perchloric acid / 3 h / 20 °C
10.2: pH 8
11.1: potassium carbonate / tetrakis(triphenylphosphine) palladium(0) / 1,2-dimethoxyethane / 0.33 h / 110 °C / Inert atmosphere; Microwave irradiation
12.1: water; lithium hydroxide monohydrate / tetrahydrofuran; methanol / 50 °C
With
n-butyllithium; perchloric acid; lithium hydroxide monohydrate; tetrabutyl ammonium fluoride; water; Pyridine hydrobromide; boron tribromide; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; 2,3-dicyano-5,6-dichloro-p-benzoquinone; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole;
dmap; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; tetrakis(triphenylphosphine) palladium(0);
In
tetrahydrofuran; methanol; 1,2-dimethoxyethane; ethanol; hexane; dichloromethane; water; toluene;