Multi-step reaction with 9 steps
1.1: boron tribromide / dichloromethane / 1 h / -78 - 20 °C
2.1: hydrogen / palladium 10% on activated carbon / N,N-dimethyl-formamide; methanol / 20 °C / 2206.72 Torr
3.1: iodine / 1-methyl-pyrrolidin-2-one / 72 h / 110 °C / Sealed tube
4.1: potassium carbonate / N,N-dimethyl-formamide / 50 °C
5.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.5 h / 0 °C
5.2: 0 °C
6.1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 50 °C
7.1: 1,1'-azodicarbonyl-dipiperidine; tributylphosphine / benzene / 1 h / 20 °C / Inert atmosphere
8.1: hydrogenchloride / 1,4-dioxane / 20 °C
9.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 20 °C
With
hydrogenchloride; lithium aluminium tetrahydride; tributylphosphine; hydrogen; iodine; boron tribromide; potassium carbonate; N-ethyl-N,N-diisopropylamine; HATU; 1,1'-azodicarbonyl-dipiperidine;
palladium 10% on activated carbon;
In
tetrahydrofuran; 1,4-dioxane; 1-methyl-pyrrolidin-2-one; methanol; dichloromethane; N,N-dimethyl-formamide; benzene;