Multi-step reaction with 9 steps
1.1: N-ethyl-N,N-diisopropylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / N,N-dimethyl-formamide / 0.5 h / 20 °C
1.2: 3 h / 20 °C
2.1: tetrahydrofuran / 2 h / 0 - 20 °C
3.1: toluene-4-sulfonic acid / toluene / 14 h / Dean-Stark; Reflux
4.1: acetic acid; sodium cyanoborohydride / ethanol / 4 h / 50 °C
5.1: hydrogenchloride / 1,4-dioxane / 12 h / 50 °C
6.1: 3 h / 100 °C
7.1: caesium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; 1,4-dioxane / 3 h / 90 °C / Inert atmosphere
8.1: palladium diacetate; sulfuric acid; zinc; 1,1'-bis-(diphenylphosphino)ferrocene / N,N-dimethyl acetamide / 4 h / 100 °C / Inert atmosphere; Sealed tube
8.2: Phenomenex Lux-2 column / Resolution of racemate; liquid CO2
9.1: N-Bromosuccinimide / chloroform / 1.5 h / Reflux
With
hydrogenchloride; 1,1'-bis-(diphenylphosphino)ferrocene; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; N-Bromosuccinimide; sulfuric acid; palladium diacetate; sodium cyanoborohydride; caesium carbonate; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; toluene-4-sulfonic acid; acetic acid; N-ethyl-N,N-diisopropylamine; zinc;
In
tetrahydrofuran; 1,4-dioxane; ethanol; chloroform; N,N-dimethyl acetamide; water; N,N-dimethyl-formamide; toluene;
7.1: |Suzuki Coupling;
DOI:10.1021/acs.jmedchem.1c01524