Multi-step reaction with 8 steps
1.1: 1H-imidazole / N,N-dimethyl-formamide / 16 h / Inert atmosphere
2.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / benzene / 2 h / Inert atmosphere; Reflux
3.1: tetrabutylammonium acetate; cesium fluoride; 18-crown-6 ether; (5aR,10bS)-2-(2,6-diethylphenyl)-4,5a,6,10b-tetrahydroindeno[2,1-b][1,2,4]triazolo[4,3-d][1,4]oxazin-2-ium tetrafluoroborate / tetrahydrofuran / 12 h / -18 °C / Inert atmosphere
4.1: sulfuric acid / 1.5 h / 75 °C
5.1: triethylamine / dichloromethane / 1.5 h / -20 °C / Inert atmosphere
6.1: palladium diacetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / tetrahydrofuran / 0.42 h / 140 °C
7.1: lithium hydroxide monohydrate / water; tetrahydrofuran / 16 h / 21 °C / Inert atmosphere
8.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / N,N-dimethyl-formamide / 16 h / Inert atmosphere
8.2: Inert atmosphere
With
1H-imidazole; N-Bromosuccinimide; 18-crown-6 ether; lithium hydroxide monohydrate; 2,2'-azobis(isobutyronitrile); sulfuric acid; (5aR,10bS)-2-(2,6-diethylphenyl)-4,5a,6,10b-tetrahydroindeno[2,1-b][1,2,4]triazolo[4,3-d][1,4]oxazin-2-ium tetrafluoroborate; tetrabutylammonium acetate; palladium diacetate; caesium carbonate; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; triethylamine; cesium fluoride;
In
tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; benzene;
DOI:10.1021/ja405833m