Multi-step reaction with 11 steps
1.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 2 h / 20 °C
2.1: triethylamine / dichloromethane / 1 h / 0 - 20 °C
3.1: magnesium / iodine / tetrahydrofuran / 1.75 h / 60 °C
3.2: 1 h / 0 °C
4.1: boron tribromide / dichloromethane / 0.5 h / -78 - 0 °C
4.2: -78 °C
5.1: pyridinium p-toluenesulfonate / dichloromethane / 1 h / 20 °C
6.1: piperidine; 1,8-diazabicyclo[5.4.0]undec-7-ene / 2-methyl-propan-1-ol / 1.5 h / Dean-Stark trap; Reflux
7.1: tetrahydrofuran / 2.25 h / 0 - 20 °C
7.2: 0 °C
8.1: water; acetic acid / tetrahydrofuran / 90 °C
9.1: pyridinium p-toluenesulfonate / dichloromethane / 3 h / 20 °C
10.1: potassium carbonate; [2,2]bipyridinyl; copper(l) iodide / 140 °C / Inert atmosphere
11.1: water; acetic acid / 0.25 h / 90 °C
With
piperidine; [2,2]bipyridinyl; copper(l) iodide; oxalyl dichloride; water; boron tribromide; potassium carbonate; magnesium; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine;
iodine; pyridinium p-toluenesulfonate; N,N-dimethyl-formamide;
In
tetrahydrofuran; dichloromethane; 2-methyl-propan-1-ol;