Multi-step reaction with 7 steps
1.1: 0.5 h / 65 °C
2.1: bromine / acetonitrile / -6 °C
3.1: triethylamine; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane / trifuran-2-yl-phosphane; dichlorobis(tri(2-furyl)phosphine)palladium(II) / acetonitrile / 6 h / 81 - 83 °C / Inert atmosphere
3.2: 2 h / 76 - 77 °C / Inert atmosphere
3.3: 70 °C
4.1: sodium hydroxide; water / 1-methyl-pyrrolidin-2-one / 10 h / 50 - 53 °C / Inert atmosphere
4.2: 0.5 h / 45 °C / pH 5.5 - 7.5
5.1: thionyl chloride / 1-methyl-pyrrolidin-2-one / tetrahydrofuran / 1 h / 25 °C
5.2: 25 °C
6.1: sodium hydroxide; water / tetrahydrofuran; methanol / 1 h / 65 - 68 °C
6.2: 2.5 h / 60 °C
7.1: sodium hydroxide / water; tetrahydrofuran / 1.5 h / 25 - 35 °C / pH 9 - 11
With
thionyl chloride; water; bromine; triethylamine; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane; sodium hydroxide;
1-methyl-pyrrolidin-2-one; trifuran-2-yl-phosphane; dichlorobis(tri(2-furyl)phosphine)palladium(II);
In
tetrahydrofuran; 1-methyl-pyrrolidin-2-one; methanol; water; acetonitrile;
3.1: Suzuki Coupling / 3.2: Suzuki Coupling;