Multi-step reaction with 13 steps
1.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 0 - 20 °C
2.1: n-butyllithium / tetrahydrofuran; hexanes / 0.5 h / -78 °C / Inert atmosphere
2.2: 3 h / -78 °C
2.3: 16 h / 20 °C
3.1: leutidine / 12 h / 0 - 20 °C
4.1: collidine / dimethyl sulfoxide / 0.75 h / 150 °C
5.1: sodium ethanolate / ethanol / 20 h / 55 °C
5.2: 0.33 h
6.1: trifluoroacetic acid / dichloromethane / 1 h / 0 - 20 °C
7.1: dmap; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 1 h / 0 - 20 °C
8.1: 1,3-dimethylbarbituric acid / tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 1 h / 90 °C
9.1: triethylamine / dichloromethane / 2 h / 0 - 20 °C
10.1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide / 12 h / 90 °C / Inert atmosphere
11.1: formic acid / 0.5 h / 100 °C
12.1: pyridine / ethanol / 4 h / 80 °C / Inert atmosphere
13.1: water; lithium hydroxide monohydrate / tetrahydrofuran; methanol / 1 h / 0 - 20 °C
With
pyridine; dmap; n-butyllithium; formic acid; 1,3-dimethylbarbituric acid; lithium hydroxide monohydrate; water; sodium ethanolate; caesium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid;
bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0);
In
tetrahydrofuran; methanol; hexanes; ethanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;
10.1: Sonogashira Coupling;