Multi-step reaction with 13 steps
1.1: diethylamino-sulfur trifluoride / dichloromethane / 3 h / -78 - 20 °C / Inert atmosphere
1.2: 0.75 h / -40 - 20 °C / Inert atmosphere
2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 0.67 h / -55 °C / Inert atmosphere
2.2: 5 h / 20 °C / Inert atmosphere
3.1: trifluoroacetic acid / water / 14 h / 20 °C / Inert atmosphere
4.1: N-ethyl-N,N-diisopropylamine; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / N,N-dimethyl-formamide; dichloromethane / 0.25 h / -3 °C / Inert atmosphere
4.2: 26 h / Inert atmosphere
5.1: diethylamino-sulfur trifluoride / dichloromethane / 3.5 h / -78 °C / Inert atmosphere
5.2: 2 h / -78 - 20 °C / Inert atmosphere
6.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; pyridine / acetonitrile; tetrachloromethane / 72 h / -60 - 20 °C / Inert atmosphere; Darkness
7.1: trifluoroacetic acid; methoxybenzene / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere
8.1: N-ethyl-N,N-diisopropylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / dichloromethane / 0.42 h / 0 °C / Inert atmosphere
8.2: 48 h / 20 °C / Inert atmosphere
9.1: bis(dibenzylideneacetone)-palladium(0); morpholine / dichloromethane / 4 h / 20 °C / Inert atmosphere
10.1: N-ethyl-N,N-diisopropylamine; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / N,N-dimethyl-formamide; dichloromethane / 24 h / 20 °C / Inert atmosphere
11.1: triphenylphosphine; 2,6-dimethylpyridine / 7 h / 60 °C / Inert atmosphere
12.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; Bromotrichloromethane / dichloromethane / 8 h / -70 - 20 °C / Inert atmosphere
13.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; copper(l) chloride / N,N-dimethyl-formamide; dichloromethane / 30 h / 20 °C / Inert atmosphere
With
morpholine; pyridine; 2,6-dimethylpyridine; Bromotrichloromethane; diethylamino-sulfur trifluoride; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; methoxybenzene; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; triphenylphosphine; trifluoroacetic acid; copper(l) chloride; bis(dibenzylideneacetone)-palladium(0);
In
tetrachloromethane; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1002/ejoc.201600994