Multi-step reaction with 12 steps
1: bis(triphenylphosphine)palladium dibromide; sodium carbonate / ethanol; toluene
2: 1H-imidazole / N,N-dimethyl-formamide
3: tris-(dibenzylideneacetone)dipalladium(0); 1,1'-bis(di-tertbutylphosphino)ferrocene; sodium t-butanolate / tetrahydrofuran
4: magnesium; lithium chloride / tetrahydrofuran
5: water; pyridinium p-toluenesulfonate / acetone
6: lithium borohydride / tetrahydrofuran
7: tetrabutyl ammonium fluoride / tetrahydrofuran
8: triethylamine / dichloromethane
9: tetra-(n-butyl)ammonium iodide / N,N-dimethyl-formamide
10: sodium tetrahydroborate; cobalt(II) chloride hexahydrate / methanol
11: N-ethyl-N,N-diisopropylamine / dichloromethane
12: hydrogenchloride / 1,4-dioxane; dichloromethane
With
1H-imidazole; hydrogenchloride; sodium tetrahydroborate; tris-(dibenzylideneacetone)dipalladium(0); lithium borohydride; 1,1'-bis(di-tertbutylphosphino)ferrocene; bis(triphenylphosphine)palladium dibromide; cobalt(II) chloride hexahydrate; tetrabutyl ammonium fluoride; water; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; sodium carbonate; magnesium; triethylamine; N-ethyl-N,N-diisopropylamine; lithium chloride; sodium t-butanolate;
In
tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; acetone; toluene;
1: Suzuki coupling / 3: Buchwald-Hartwig α-arylation;
DOI:10.1016/j.bmcl.2012.01.044