Multi-step reaction with 11 steps
1.1: sodium hydrogencarbonate / ethyl acetate; water
2.1: pyridine / dichloromethane / 1 h / Cooling with ice
3.1: lithium chloride / bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide / 1 h / 95 °C / Inert atmosphere
4.1: hydrogen / palladium 10% on activated carbon / ethanol / 4 h
5.1: N-Bromosuccinimide / acetonitrile / 1 h / 20 °C
6.1: trifluoroacetic acid / dichloromethane / 0.5 h / 20 °C
7.1: caesium carbonate / palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / toluene / 1 h / 100 °C / Inert atmosphere
8.1: sulfuric acid / methanol / 100 h / 20 °C / Reflux
9.1: pyridine / dichloromethane / 2 h / 20 °C
10.1: tris-(dibenzylideneacetone)dipalladium(0); di-tert-butylneopentylphosphonium tetrafluoroborate / 1,4-dioxane; dimethyl sulfoxide / 1 h / 95 °C / Inert atmosphere
11.1: water; lithium hydroxide monohydrate / 1,4-dioxane / 1.25 h / 110 °C / microwave irradiation
11.2: pH 4 - 5
With
pyridine; N-Bromosuccinimide; lithium hydroxide monohydrate; sulfuric acid; water; hydrogen; sodium hydrogencarbonate; caesium carbonate; trifluoroacetic acid; lithium chloride;
bis-triphenylphosphine-palladium(II) chloride; tris-(dibenzylideneacetone)dipalladium(0); di-tert-butylneopentylphosphonium tetrafluoroborate; palladium 10% on activated carbon; palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl;
In
1,4-dioxane; methanol; ethanol; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile;