Multi-step reaction with 11 steps
1.1: 1H-imidazole / dichloromethane / 4 h / 0 °C
2.1: n-butyllithium / tetrahydrofuran; hexane / 0.75 h / -78 °C / Inert atmosphere
2.2: 1 h / -78 °C / Inert atmosphere
3.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane; acetonitrile / 1 h / -78 °C
4.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.75 h / 0 °C
4.2: 3 h / 0 °C
5.1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine; triphenylphosphine / N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere
6.1: toluene-4-sulfonic acid / methanol / 8 h / 0 - 20 °C
7.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 6 h / Reflux
8.1: sodium chlorite; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene / water; tert-butyl alcohol / 10 h / 20 °C
9.1: methanol; hexane; toluene / 0.33 h / 0 °C
10.1: dichloro bis(acetonitrile) palladium(II) / acetonitrile / 8 h / 20 °C / Inert atmosphere
11.1: indium(III) chloride / acetonitrile / 5 h / 20 °C / Inert atmosphere
With
1H-imidazole; triethylsilane; indium(III) chloride; bis-triphenylphosphine-palladium(II) chloride; dichloro bis(acetonitrile) palladium(II); sodium chlorite; copper(l) iodide; n-butyllithium; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene; boron trifluoride diethyl etherate; sodium hydride; toluene-4-sulfonic acid; triethylamine; triphenylphosphine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione;
In
tetrahydrofuran; methanol; hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile; mineral oil; tert-butyl alcohol;
5.1: Sonogashira coupling;
DOI:10.1002/chem.201103604