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: triphenylphosphine / methanol; water / 17 h
11.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.25 h / 0 °C
11.2: 16.17 h / 0 - 20 °C
12.1: Hoveyda-Grubbs catalyst second generation / 1,2-dichloro-ethane / 90 °C
13.1: hydrogen / palladium on activated charcoal / ethanol / 25 °C / 759.83 Torr
With
2-hydroxypyridin; hydrogenchloride; dipyridinium dichromate; di-isopropyl azodicarboxylate; sulfuric acid; water; hydrogen; boron tribromide; potassium carbonate; magnesium; N-ethyl-N,N-diisopropylamine; triphenylphosphine; HATU; silver(l) oxide;
Hoveyda-Grubbs catalyst second generation; palladium on activated charcoal; iodine;
In
tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide;