Multi-step reaction with 10 steps
1.1: dmap; triethylamine / 9.5 h / 20 °C
2.1: silver nitrate; triethylamine / tetrahydrofuran; N,N-dimethyl-formamide / 0.17 h / 0 °C
2.2: 12 h / 0 - 20 °C
3.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 3.33 h / -78 - -20 °C
4.1: quinoline; hydrogen / ethyl acetate / 2 h / 20 °C
5.1: dimethyl sulfoxide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / 4 h / 20 °C
6.1: sodium dihydrogenphosphate; sodium chlorite; 2-methyl-but-2-ene / water; tert-butyl alcohol / 0.83 h / 0 °C
7.1: benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 8 h / 0 - 20 °C
8.1: tris-(dibenzylideneacetone)dipalladium(0); ((diphenylphosphoryl)oxy)copper(I); triethyl phosphite / tetrahydrofuran; hexane / 20 °C
9.1: cerium(III) chloride heptahydrate / ethanol / 0.33 h / 20 °C
9.2: 1.5 h / -40 °C
10.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2.5 h / 20 - 50 °C
With
quinoline; triethylsilane; dmap; sodium chlorite; tris-(dibenzylideneacetone)dipalladium(0); sodium dihydrogenphosphate; 2-methyl-but-2-ene; ((diphenylphosphoryl)oxy)copper(I); cerium(III) chloride heptahydrate; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; hydrogen; silver nitrate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; triethyl phosphite; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione;
In
tetrahydrofuran; ethanol; hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; tert-butyl alcohol;
8.1: Stille-type coupling;
DOI:10.1016/j.tet.2010.11.017