Multi-step reaction with 9 steps
1: sulfuric acid; nitric acid / 3 h / -10 - 0 °C
2: di-tert-butyl-diazodicarboxylate; triphenylphosphine / dichloromethane / 0 - 20 °C
3: iron; acetic acid / 2 h / 65 °C
4: tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 60 °C
5: hydrogen; pyridinium p-toluenesulfonate / ethyl acetate / 20 °C
6: trifluoroacetic acid / dichloromethane / 0 - 20 °C
7: di-tert-butyl-diazodicarboxylate; triphenylphosphine / dichloromethane / 0 - 20 °C
8: formic acid / water / 85 °C
9: ammonia / methanol / 48 h / 70 °C
With
tris-(dibenzylideneacetone)dipalladium(0); formic acid; di-tert-butyl-diazodicarboxylate; sulfuric acid; ammonia; hydrogen; nitric acid; pyridinium p-toluenesulfonate; iron; caesium carbonate; acetic acid; triphenylphosphine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; trifluoroacetic acid;
In
1,4-dioxane; methanol; dichloromethane; water; ethyl acetate;
2: Mitsunobu reaction / 4: Buchwald-Hartwig reaction / 7: Mitsunobu reaction;
DOI:10.1021/jm1011726