Multi-step reaction with 9 steps
1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.33 h / 0 °C
1.2: 0 °C
2.1: n-butyllithium / tetrahydrofuran / 1.5 h / -78 °C
2.2: 1 h / -78 - 0 °C
3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 0 °C
4.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 - 5 °C
5.1: copper(l) iodide / N,N-dimethyl-formamide / 2 h / 100 °C
6.1: n-butyllithium / tetrahydrofuran / 0.5 h / -45 - 40 °C
7.1: palladium diacetate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; caesium carbonate / 1,4-dioxane; water / 12 h / 60 °C
8.1: palladium diacetate; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 12 h / 100 °C / Inert atmosphere
9.1: hydrogenchloride / tetrahydrofuran; 1,4-dioxane / 5 h / Reflux
With
dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; hydrogenchloride; copper(l) iodide; n-butyllithium; tetrabutyl ammonium fluoride; palladium diacetate; sodium hydride; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene;
In
tetrahydrofuran; 1,4-dioxane; water; N,N-dimethyl-formamide; mineral oil;
DOI:10.1021/jm3016014