Multi-step reaction with 9 steps
1.1: bromine / dichloromethane / 36 h / 0 - 20 °C / Inert atmosphere
2.1: triethylamine / palladium diacetate; (diphenylphosphin)ferrocene / diethyl ether; ethanol / 70 °C / Inert atmosphere
2.2: 2 h
3.1: bromine; pyridine / dichloromethane / 2 h / 0 - 20 °C
3.2: 5 °C
4.1: boron trifluoride diethyl etherate / toluene; 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran; methanol / 20 °C / Inert atmosphere
4.2: 12 h / 90 °C
5.1: sodium hydroxide / methanol / 16 h / 23 °C
5.2: pH 3
6.1: bis-triphenylphosphine-palladium(II) chloride / 1,4-dioxane / 3 h / 100 °C / Inert atmosphere
6.2: 0.42 h / 50 °C
7.1: O-(N-succinimidyl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.25 h / 20 °C
7.2: 1 h
8.1: triethylamine; titanium tetrachloride / dichloromethane / 48 h / 10 - 23 °C / Inert atmosphere
9.1: sodium cyanoborohydride; acetic acid / dichloromethane; methanol / 0.5 h / 20 °C
With
pyridine; boron trifluoride diethyl etherate; bromine; titanium tetrachloride; sodium cyanoborohydride; O-(N-succinimidyl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; sodium hydroxide;
bis-triphenylphosphine-palladium(II) chloride; (diphenylphosphin)ferrocene; palladium diacetate;
In
1,4-dioxane; methanol; diethyl ether; ethanol; dichloromethane; 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran; toluene;