Multi-step reaction with 12 steps
1: 1 h / 130 °C
2: sodium cyanoborohydride / acetic acid / 24 h / 20 °C
3: sodium hydrogencarbonate / 24 h / 0 - 20 °C
4: hydrogenchloride / methanol / 24 h / Reflux
5: Dess-Martin periodane / dichloromethane / 20 °C
6: tetrahydrofuran / -78 °C
7: lithium hydroxide; water / tetrahydrofuran / 12 h / 20 °C
8: isopropyl chloroformate; triethylamine / 3 h
9: trichlorophosphate / acetonitrile / 15 h / 20 °C
10: N-Bromosuccinimide / N,N-dimethyl-formamide / 1 h / 20 °C
11: isopropyl alcohol / 7 h / 100 °C / Sealed tube
12: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / 1,4-dioxane / 2 h / 100 °C
With
hydrogenchloride; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; N-Bromosuccinimide; water; sodium cyanoborohydride; sodium hydrogencarbonate; potassium carbonate; Dess-Martin periodane; isopropyl chloroformate; triethylamine; lithium hydroxide; trichlorophosphate;
In
tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; acetic acid; N,N-dimethyl-formamide; isopropyl alcohol; acetonitrile;
12: |Suzuki Coupling;
DOI:10.1016/j.bmcl.2020.127390