Multi-step reaction with 9 steps
1.1: sodium nitrite; hydrogenchloride / water / 1 h / 0 °C
1.2: 1 h / 0 °C
2.1: dichloromethane; methanol / 3 h / 20 °C
2.2: 22 h / 0 - 50 °C
2.3: 0 °C
3.1: 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate / toluene / 16 h / Inert atmosphere; Reflux
4.1: bis-triphenylphosphine-palladium(II) chloride / toluene / 16 h / 110 °C
5.1: water; hydrogenchloride / tetrahydrofuran / 2 h / 20 °C
6.1: sodium hydride / 1,2-dimethoxyethane; mineral oil / 0.25 h / Inert atmosphere; Microwave irradiation
7.1: acetic acid; hydrazine / 1.5 h / 90 °C
8.1: N,N-dimethyl-formamide / 1 h / 90 °C
9.1: palladium 10% on activated carbon; hydrogen / methanol; tetrahydrofuran / 1 h / 20 °C
With
hydrogenchloride; bis-triphenylphosphine-palladium(II) chloride; tris-(dibenzylideneacetone)dipalladium(0); palladium 10% on activated carbon; water; hydrogen; sodium hydride; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; acetic acid; hydrazine; sodium nitrite;
In
tetrahydrofuran; methanol; 1,2-dimethoxyethane; dichloromethane; water; N,N-dimethyl-formamide; toluene; mineral oil;