Multi-step reaction with 13 steps
1: pyridine / dichloromethane / 2 h / 20 °C / Inert atmosphere
2: N-ethyl-N,N-diisopropylamine / dichloromethane / 0 - 20 °C
3: palladium diacetate; 1,3-bis-(diphenylphosphino)propane; triethylamine / ethylene glycol / 6 h / 120 °C / Inert atmosphere
4: hydrogenchloride / water; 1,4-dioxane / 1 h / 20 °C
5: pyridinium hydrobromide perbromide / tetrahydrofuran / 0.25 h / 80 °C / Microwave irradiation
6: ethanol / 0.33 h / 60 °C / Microwave irradiation
7: N-Bromosuccinimide / dichloromethane / 0.5 h / 20 °C
8: N,N-dimethyl-formamide / 16 h / 20 °C
9: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate / 1,2-dimethoxyethane; water / 1 h / 110 °C / Microwave irradiation
10: ethylenediamine / ethanol / 8 h / Reflux
11: copper(ll) bromide; tert.-butylnitrite / acetonitrile / 8 h / 85 °C
12: trifluoroacetic acid / water / 6 h / 80 °C
13: N,N-dimethyl acetamide / 3 h / 120 °C / Microwave irradiation
With
pyridine; hydrogenchloride; N-Bromosuccinimide; tert.-butylnitrite; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; 1,3-bis-(diphenylphosphino)propane; palladium diacetate; caesium carbonate; pyridinium hydrobromide perbromide; ethylenediamine; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; copper(ll) bromide;
In
tetrahydrofuran; 1,4-dioxane; 1,2-dimethoxyethane; ethanol; dichloromethane; N,N-dimethyl acetamide; water; ethylene glycol; N,N-dimethyl-formamide; acetonitrile;
3: |Heck Reaction / 9: |Suzuki Coupling / 11: |Sandmeyer Reaction;
DOI:10.1002/cmdc.201402424