Multi-step reaction with 9 steps
1.1: triethylamine / palladium diacetate; (diphenylphosphin)ferrocene / diethyl ether; ethanol / 70 °C / Inert atmosphere
1.2: 2 h
2.1: bromine; pyridine / dichloromethane / 2 h / 0 - 20 °C
2.2: 5 °C
3.1: boron trifluoride diethyl etherate / toluene; 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran; methanol / 20 °C / Inert atmosphere
3.2: 12 h / 90 °C
4.1: bis-triphenylphosphine-palladium(II) chloride / 1,4-dioxane / 90 °C / Inert atmosphere
4.2: 0.5 h / 45 °C
5.1: sodium tetrahydroborate / dichloromethane; methanol / 0.25 h / -10 °C
6.1: phosphorus tribromide / dichloromethane / 36 h / 20 °C / Inert atmosphere; Cooling with ice
6.2: pH 6 / Cooling with ice
7.1: dichloromethane / 32 h / 20 - 50 °C
8.1: sodium hydroxide / tetrahydrofuran; methanol / 24 h / 20 - 50 °C
8.2: pH 3
9.1: 4-methyl-morpholine / 1-methyl-pyrrolidin-2-one / 2 h / 20 °C
With
4-methyl-morpholine; pyridine; sodium tetrahydroborate; boron trifluoride diethyl etherate; bromine; phosphorus tribromide; triethylamine; sodium hydroxide;
bis-triphenylphosphine-palladium(II) chloride; (diphenylphosphin)ferrocene; palladium diacetate;
In
tetrahydrofuran; 1,4-dioxane; 1-methyl-pyrrolidin-2-one; methanol; diethyl ether; ethanol; dichloromethane; 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran; toluene;