Multi-step reaction with 8 steps
1.1: n-butyllithium; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 3.5 h / -78 - 0 °C
1.2: 1.5 h / -78 °C
2.1: hydrazine hydrate / 1,2-dimethoxyethane / 20 - 75 °C
3.1: iodine; potassium hydroxide / 1,4-dioxane / 4 h / 75 °C
4.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C
4.2: 19 h / 20 °C
5.1: sodium hydride / tetrahydrofuran / 0.5 h / 20 °C
5.2: 4 h / Reflux
6.1: potassium acetate / di-tert-butyl[dichloro({di-tert-butyl[4-(dimethylamino)phenyl]phosphaniumyl})palladio][4-(dimethylamino)phenyl]phosphanium / tetrahydrofuran; acetonitrile / 0.67 h / 145 °C / Inert atmosphere; Microwave irradiation
7.1: lithium hydroxide / tetrahydrofuran / 12 h / Reflux
7.2: 20 °C / pH 7
8.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 25 °C
With
n-butyllithium; iodine; potassium acetate; sodium hydride; hydrazine hydrate; N-ethyl-N,N-diisopropylamine; HATU; potassium hydroxide; lithium hydroxide;
di-tert-butyl[dichloro({di-tert-butyl[4-(dimethylamino)phenyl]phosphaniumyl})palladio][4-(dimethylamino)phenyl]phosphanium;
In
tetrahydrofuran; 1,4-dioxane; 1,2-dimethoxyethane; N,N-dimethyl-formamide; acetonitrile; mineral oil;