Multi-step reaction with 18 steps
1.1: methanol; toluene / Cooling with ice
2.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / water; ethanol; toluene / 6 h / 100 °C / Sealed tube; Inert atmosphere
3.1: diisobutylaluminium hydride / dichloromethane; toluene / 2.5 h / -78 - 20 °C
4.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1.5 h / 20 °C
5.1: tetrahydrofuran / 0 °C
6.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 20 °C
7.1: boron tribromide / dichloromethane / 1 h / 20 °C
8.1: pyrrolidine / methanol / 8 h / 100 °C / Molecular sieve; Sealed tube
9.1: sodium tetrahydroborate / tetrahydrofuran; methanol / 0.75 h / 20 °C
10.1: methanesulfonyl chloride; triethylamine / dichloromethane / 0 - 20 °C
10.2: 36 h / 20 °C
11.1: palladium 10% on activated carbon; hydrogen / ethyl acetate
12.1: hydrogenchloride / 1,4-dioxane / 3 h / 20 °C
13.1: N-[(dimethylamino)-1H-1,2,3-triazolo-[4,5-b]pyridin-1-ylmethylene]-N-methylmethanaminium hexafluorophosphate N-oxide; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C
14.1: lithium hydroxide monohydrate / water; tetrahydrofuran; methanol / 1 h / 60 °C
15.1: N-[(dimethylamino)-1H-1,2,3-triazolo-[4,5-b]pyridin-1-ylmethylene]-N-methylmethanaminium hexafluorophosphate N-oxide; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 48 h / 20 °C
16.1: 1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene[2-(iso-propoxy)-5-(N,N-dimethylaminosulfonyl)phenyl]methylene ruthenium(II) dichloride; p-benzoquinone / 1,2-dichloro-ethane / 3 h / 65 °C / Inert atmosphere
17.1: lithium hydroxide monohydrate / water; tetrahydrofuran; methanol / 1 h / 60 °C
18.1: 1,1'-carbonyldiimidazole / tetrahydrofuran / 2 h / Reflux
18.2: 58 h / 20 - 50 °C
With
pyrrolidine; hydrogenchloride; sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium(0); lithium hydroxide monohydrate; 1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene[2-(iso-propoxy)-5-(N,N-dimethylaminosulfonyl)phenyl]methylene ruthenium(II) dichloride; palladium 10% on activated carbon; N-[(dimethylamino)-1H-1,2,3-triazolo-[4,5-b]pyridin-1-ylmethylene]-N-methylmethanaminium hexafluorophosphate N-oxide; hydrogen; boron tribromide; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; Dess-Martin periodane; methanesulfonyl chloride; triethylamine; N-ethyl-N,N-diisopropylamine; 1,1'-carbonyldiimidazole; p-benzoquinone;
In
tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; water; ethyl acetate; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene;