Multi-step reaction with 14 steps
1: acetic acid; zinc / water / 1.83 h / 80 - 85 °C
2: glyoxylic acid ethyl ester; magnesium sulfate / dichloromethane / 0 - 20 °C
3: dmap; triethylamine / toluene / 18 h / 70 °C
4: ammonium cerium (IV) nitrate / water; acetonitrile / 0.25 h / -15 °C
5: dichloromethane / 4 h / 20 °C
6: copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine / 1,4-dioxane / 21 h / 100 °C
7: tetrabutyl ammonium fluoride / tetrahydrofuran; water / 0.33 h / 0 °C
8: hydrogen bromide; acetic acid / tetrahydrofuran / 0.5 h / 0 °C
9: tetrakis(triphenylphosphine) palladium(0); sodium ethanolate; caesium carbonate / 1,4-dioxane / 4 h / 100 °C
10: lithium borohydride / tetrahydrofuran / 0 - 20 °C
11: dmap; triethylamine / dichloromethane / 10 h / 20 °C
12: sodium azide / N,N-dimethyl-formamide / 4 h / 80 °C
13: trifluoroacetic acid / dichloromethane / 2 h / 0 °C
14: dmap; triethylamine / toluene / 0 - 40 °C
With
dmap; copper(l) iodide; lithium borohydride; tetrakis(triphenylphosphine) palladium(0); sodium azide; glyoxylic acid ethyl ester; ammonium cerium (IV) nitrate; tetrabutyl ammonium fluoride; hydrogen bromide; sodium ethanolate; magnesium sulfate; caesium carbonate; acetic acid; triethylamine; trifluoroacetic acid; zinc;
In
tetrahydrofuran; 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile;
6: Sonogashira coupling / 9: Suzuki-Miyaura cross-coupling reaction;
DOI:10.1002/ejoc.201100242