Multi-step reaction with 11 steps
1.1: triethylamine; pyridine; diammonium sulfide / 4 h / 50 °C
2.1: N,N-dimethyl-formamide / 18 h / 20 °C
2.2: 4 h / 120 °C
3.1: lithium borohydride; methanol / 0 °C
4.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 20 - 70 °C
5.1: dichloromethane / 0 - 20 °C
6.1: water; lithium hydroxide / methanol / 24 h / 20 °C
6.2: pH 5
7.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 2 h / 20 °C
8.1: sodium azide / 1,4-dioxane; water; acetone / 1.25 h / 0 °C
9.1: 1,4-dioxane; diphenyl ether-biphenyl eutectic / 1.25 h / 230 °C
10.1: phosphorus(V) oxybromide / acetonitrile / 2 h / 100 °C
11.1: caesium carbonate / 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 2 h / 160 °C / Inert atmosphere; Microwave irradiation
With
pyridine; methanol; diammonium sulfide; lithium borohydride; sodium azide; oxalyl dichloride; water; caesium carbonate; triethylamine; lithium hydroxide; phosphorus(V) oxybromide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione;
tris-(dibenzylideneacetone)dipalladium(0); N,N-dimethyl-formamide; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene;
In
1,4-dioxane; methanol; diphenyl ether-biphenyl eutectic; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; acetonitrile;