Multi-step reaction with 13 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: sodium hexamethyldisilazane / tetrahydrofuran / 1.25 h / -50 - 0 °C / Inert atmosphere
4.2: 24 h / -20 - 20 °C
4.3: -50 °C
5.1: potassium carbonate / acetone / 2 h / 60 °C / Inert atmosphere
6.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 20 °C
7.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / 10 - 20 °C / Inert atmosphere
8.1: bis-triphenylphosphine-palladium(II) chloride / 1,4-dioxane / 4 h / 90 °C / Inert atmosphere
8.2: 1 h / 20 °C
9.1: sodium tetrahydroborate / dichloromethane; methanol / 0.25 h / -10 °C
10.1: sodium hydroxide; water / methanol / 1 h / 20 °C
10.2: pH 2 - 3
11.1: O-(N-succinimidyl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 10 - 20 °C / Inert atmosphere
11.2: 10 - 20 °C
12.1: phosphorus tribromide / 1,2-dichloro-ethane / 1 h / 10 - 50 °C / Inert atmosphere
13.1: ISOPROPYLAMIDE / 4 h / 20 °C
With
pyridine; sodium tetrahydroborate; water; bromine; sodium hexamethyldisilazane; phosphorus tribromide; potassium carbonate; O-(N-succinimidyl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; sodium hydroxide;
bis-triphenylphosphine-palladium(II) chloride; (diphenylphosphin)ferrocene; palladium diacetate;
In
tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; ethanol; dichloromethane; ISOPROPYLAMIDE; 1,2-dichloro-ethane; acetone;