Multi-step reaction with 15 steps
1.1: hydrogen; palladium 10% on activated carbon / ethanol; ethyl acetate / 24 h / 760.05 Torr
2.1: sulfuric acid; 3-Nitrobenzenesulfonic acid; boric acid; ferrous(II) sulfate heptahydrate / 1 h / 140 °C
3.1: sulfuric acid; N-Bromosuccinimide / 3.5 h / 15 °C
4.1: boron tribromide / dichloromethane / 3 h
4.2: 12 h / pH 12
5.1: pyridine / dichloromethane / 2 h / -30 - 0 °C
6.1: lithium chloride; bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide / 16 h / 80 °C
7.1: AD-mix α / water; tert-butyl alcohol / 48 h / 0 °C
8.1: pyridine / dichloromethane / 12 h / 0 - 20 °C
8.2: 2 h / 25 °C
9.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 12 h
10.1: 10 h / 140 °C
11.1: methylamine / ethanol; water / 1.33 h / 78 °C
12.1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / water; 1,2-dimethoxyethane / 90 °C / Inert atmosphere
13.1: copper(l) iodide; 8-quinolinol; potassium carbonate / dimethyl sulfoxide / 22 h / 125 °C
14.1: sodium hydroxide / methanol; water; tetrahydrofuran / 24 h / 40 °C
15.1: chromium(VI) oxide; periodic acid / water; acetonitrile / 2 h
With
pyridine; chromium(VI) oxide; ferrous(II) sulfate heptahydrate; bis-triphenylphosphine-palladium(II) chloride; N-Bromosuccinimide; copper(l) iodide; 8-quinolinol; tetrakis(triphenylphosphine) palladium(0); AD-mix α; sulfuric acid; palladium 10% on activated carbon; hydrogen; boric acid; boron tribromide; potassium carbonate; periodic acid; 3-chloro-benzenecarboperoxoic acid; 3-Nitrobenzenesulfonic acid; methylamine; lithium chloride; sodium hydroxide;
In
tetrahydrofuran; methanol; 1,2-dimethoxyethane; ethanol; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol;