Multi-step reaction with 9 steps
1.1: dmap / tetrahydrofuran / 16 h / 20 °C
2.1: caesium carbonate / Pd tetrakis / 1,2-dimethoxyethane; water / 22 h / Heating; Reflux
3.1: hydrogenchloride / ethyl acetate
4.1: caesium carbonate / acetonitrile / 2 h / Reflux
5.1: hydrazine hydrate / methanol / 16 h / 75 °C
6.1: HATU / tetrahydrofuran; N,N-dimethyl-formamide / 24 h / 20 °C
7.1: N-Bromosuccinimide / tetrahydrofuran / 3 h / 70 °C
8.1: N-Bromosuccinimide / bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide / 0.37 h / 120 °C / Irradiation with 150 W microwave
9.1: osmium(VIII) oxide / 1,4-dioxane; water; tert-butyl alcohol / 0.03 h
9.2: 48 h / 20 °C
With
hydrogenchloride; dmap; N-Bromosuccinimide; osmium(VIII) oxide; caesium carbonate; hydrazine hydrate; HATU;
bis-triphenylphosphine-palladium(II) chloride;
In
tetrahydrofuran; 1,4-dioxane; methanol; 1,2-dimethoxyethane; water; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol;