Multi-step reaction with 17 steps
1: potassium carbonate / methanol / 1.5 h / 20 °C / Inert atmosphere
2: tris(dibenzylideneacetone)dipalladium(0) chloroform complex; triphenylphosphine; copper(l) iodide; N-butylamine / toluene / 1.17 h / Inert atmosphere; Reflux
3: sodium methylate / tetrahydrofuran; methanol / 0.5 h / 20 - 50 °C / Inert atmosphere
4: zinc; hydrogenchloride / water; methanol / 0.67 h / 20 °C / Reflux
5: sodium hydride / tetrahydrofuran; N,N-dimethyl-formamide / 0.33 h / 0 °C / Inert atmosphere
6: zinc; ammonium chloride / ethanol / 0.33 h / 20 °C
7: pyridine / dichloromethane / 2 h / 0 °C / Inert atmosphere
8: camphor-10-sulfonic acid / methanol / 0.67 h / 20 - 50 °C
9: diamide; tributylphosphine / toluene / 1.17 h / 20 °C / Inert atmosphere; Reflux
10: mercaptoacetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 0.33 h / 20 °C / Inert atmosphere
11: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0.08 h / 20 °C / Inert atmosphere
12: caesium carbonate / tetrahydrofuran; acetonitrile / 1 h / 20 - 50 °C
13: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere
14: tributylphosphine / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere
15: trifluorormethanesulfonic acid / dichloromethane / 0.33 h / -78 - 0 °C / Inert atmosphere
16: dmap; triethylamine / tetrahydrofuran; dichloromethane / 0.17 h / 20 °C / Inert atmosphere
17: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0.42 h / 20 °C / Inert atmosphere
With
pyridine; hydrogenchloride; dmap; tris(dibenzylideneacetone)dipalladium(0) chloroform complex; copper(l) iodide; tributylphosphine; trifluorormethanesulfonic acid; diamide; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; sodium methylate; sodium hydride; potassium carbonate; ammonium chloride; caesium carbonate; mercaptoacetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-butylamine; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; zinc;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile;
2: |Sonogashira Cross-Coupling;
DOI:10.1002/anie.201204726