Multi-step reaction with 12 steps
1.1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride / diethylamine / 10 h / 20 °C
2.1: dichloromethane / 1 h / 0 °C / Cooling with ice
3.1: sodium methylate / methanol / 0.5 h / 0 °C
4.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere
4.2: 0.17 h / -78 °C / Inert atmosphere
5.1: nitronium tetrafluoborate / acetonitrile / 0.17 h / 0 °C / Cooling with ice
6.1: acetic acid; zinc / ethanol; water / 0.33 h / 20 - 60 °C
7.1: triethylamine / dichloromethane / 16 h / 0 - 20 °C / Cooling with ice
8.1: sodium hydride / N,N-dimethyl-formamide / 0.33 h / 20 °C / Inert atmosphere
8.2: 1 h / 20 - 40 °C
9.1: hydrogenchloride / ethyl acetate / 0.5 h / 20 - 40 °C
10.1: sodium tris(acetoxy)borohydride / tetrahydrofuran / 0.5 h / 20 °C
11.1: tetrakis(triphenylphosphine) palladium(0); barium hydroxide octahydrate / 1,2-dimethoxyethane; water / 4 h / 90 °C / Inert atmosphere
12.1: ethyl acetate / 20 °C
With
hydrogenchloride; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); n-butyllithium; nitronium tetrafluoborate; barium hydroxide octahydrate; sodium methylate; sodium tris(acetoxy)borohydride; sodium hydride; acetic acid; triethylamine; zinc;
In
tetrahydrofuran; methanol; 1,2-dimethoxyethane; ethanol; hexane; dichloromethane; water; ethyl acetate; diethylamine; N,N-dimethyl-formamide; acetonitrile;
11.1: Suzuki coupling;
DOI:10.1021/jm300259r