Multi-step reaction with 10 steps
1.1: n-butyllithium / tetrahydrofuran / 2 h / -78 - -70 °C
1.2: 2 h / 20 °C
2.1: hydrogenchloride / dichloromethane / 0.5 h
3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 20 °C
3.2: 2 h / 20 °C
4.1: tri-n-butyl-tin hydride; 2,2'-azobis(isobutyronitrile) / toluene / 3 h / Reflux
5.1: boron tribromide / dichloromethane / 2 h / 20 °C / Cooling with ice
6.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 110 °C / Microwave irradiation
7.1: hydrazine hydrate; palladium on activated charcoal / ethanol / 3 h / Inert atmosphere; Reflux
8.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.25 h / 20 °C / Inert atmosphere
8.2: 24 h / 60 °C / Inert atmosphere
9.1: trifluoroacetic acid / dichloromethane / 2 h / 0 - 20 °C
10.1: triethylamine / dichloromethane / 1.17 h / 0 - 20 °C / Inert atmosphere
With
hydrogenchloride; n-butyllithium; 2,2'-azobis(isobutyronitrile); palladium on activated charcoal; tri-n-butyl-tin hydride; boron tribromide; sodium hydride; potassium carbonate; hydrazine hydrate; triethylamine; N-ethyl-N,N-diisopropylamine; HATU; trifluoroacetic acid;
In
tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene; mineral oil;