Multi-step reaction with 9 steps
1.1: bis(benzonitrile)palladium(II) dichloride; triethylamine / 1,4-dioxane / 24 h / 58 °C
2.1: lithium borohydride / tetrahydrofuran; methanol / 1 h / Reflux
3.1: dmap; methanesulfonyl chloride / dichloromethane / 0.17 h / 0 °C / Inert atmosphere
4.1: 0.75 h / 115 °C / Inert atmosphere
5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 20 °C
6.1: methanol / 1 h / Reflux; Inert atmosphere
7.1: sodium hydroxide / 1,4-dioxane; water / 4 h / Reflux; Inert atmosphere
8.1: N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; trichlorophosphate / 4 h / 0 °C / Inert atmosphere
9.1: tributyl-amine; bis(tri-n-butylammonium) pyrophosphate / N,N-dimethyl-formamide / 0.17 h / Inert atmosphere
9.2: 1 h / 20 °C / pH 7.5 / Inert atmosphere; aq. buffer
With
dmap; bis(benzonitrile)palladium(II) dichloride; lithium borohydride; tributyl-amine; tetrabutyl ammonium fluoride; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; bis(tri-n-butylammonium) pyrophosphate; methanesulfonyl chloride; triethylamine; sodium hydroxide; trichlorophosphate;
In
tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1002/anie.201106516