Multi-step reaction with 12 steps
1: sodium iodate; sulfuric acid; iodine; acetic acid
2: thionyl chloride / methanol / Reflux
3: sodium hydrogencarbonate / tetrahydrofuran
4: N,N-diisopropylamido-magnesium bromide; magnesium chloride / tetrahydrofuran
5: hydrogenchloride / water
6: sodium tetrahydroborate / ethanol / -78 °C
7: potassium carbonate / methanol
8: ethanol
9: sodium hydrogencarbonate / dichloromethane; water
10: hydrogenchloride / 1,4-dioxane
11: bis(trichloromethyl) carbonate; triethylamine / dichloromethane
12: palladium 10% on activated carbon; potassium carbonate / ethanol; water; toluene / 8 h / 80 °C
With
hydrogenchloride; sodium tetrahydroborate; thionyl chloride; sodium iodate; bis(trichloromethyl) carbonate; sulfuric acid; palladium 10% on activated carbon; N,N-diisopropylamido-magnesium bromide; iodine; sodium hydrogencarbonate; potassium carbonate; acetic acid; triethylamine; magnesium chloride;
In
tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; water; toluene;
12: Suzuki coupling;
DOI:10.1016/j.bmcl.2012.01.037