Multi-step reaction with 12 steps
1.1: potassium carbonate / acetone / 4 h / Reflux
2.1: diisobutylaluminium hydride / hexane; tetrahydrofuran / 3 h / -40 °C
3.1: manganese(IV) oxide / dichloromethane / 168 h / 20 °C
4.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C
4.2: 0 - 20 °C
5.1: magnesium; ethylene dibromide / tetrahydrofuran / 2.5 h / 60 - 70 °C / Inert atmosphere
5.2: 1 h / 0 °C
6.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 3 h / 0 °C
7.1: tris(dimethylamino)sulfonium trimethylsilyldifluoride / N,N-dimethyl-formamide / 0 - 20 °C
8.1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / dichloromethane / 20 °C
9.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / 1,2-dichloro-ethane / 80 °C / Inert atmosphere
10.1: palladium on activated charcoal; hydrogen / ethyl acetate / 4 h
11.1: lithium hydroxide / tetrahydrofuran; methanol / 20 °C
12.1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / dichloromethane / 20 °C
With
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; manganese(IV) oxide; palladium on activated charcoal; tris(dimethylamino)sulfonium trimethylsilyldifluoride; hydrogen; sodium hydride; diisobutylaluminium hydride; potassium carbonate; magnesium; ethylene dibromide; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; lithium hydroxide;
In
tetrahydrofuran; methanol; hexane; dichloromethane; ethyl acetate; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetone; mineral oil;
DOI:10.1016/j.bmcl.2017.11.005