Multi-step reaction with 13 steps
1.1: magnesium / iodine / tetrahydrofuran / 4 h / Heating / reflux
2.1: boron tribromide / dichloromethane / 3 h / 0 °C
3.1: potassium carbonate / N,N-dimethyl-formamide / 17 h / 20 - 110 °C
4.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 0.25 h / -15 °C
4.2: 12.5 h / -15 - 20 °C
5.1: hydrogenchloride / 3 h / 0 - 20 °C
6.1: silver(l) oxide / N,N-dimethyl-formamide / 14 h / 20 °C
7.1: sulfuric acid; water / 1,4-dioxane / 3 h / 20 °C / Heating / reflux
8.1: dipyridinium dichromate / dichloromethane / 10 h / 0 - 20 °C / Molecular sieve
9.1: 2-hydroxypyridin; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 h / 70 °C
10.1: pyridine / 12.67 h / 0 - 20 °C
11.1: potassium superoxide / 18-crown-6 ether / 1,2-dimethoxyethane; dimethyl sulfoxide / 0.5 h / 0 °C
12.1: triphenylphosphine / methanol; water / 16 h / 20 °C
13.1: triethylamine / dichloromethane / 6.5 h / 0 - 20 °C
With
pyridine; 2-hydroxypyridin; hydrogenchloride; potassium superoxide; dipyridinium dichromate; di-isopropyl azodicarboxylate; sulfuric acid; water; boron tribromide; potassium carbonate; magnesium; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; silver(l) oxide;
18-crown-6 ether; iodine;
In
tetrahydrofuran; 1,4-dioxane; methanol; 1,2-dimethoxyethane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide;