Multi-step reaction with 13 steps
1.1: sodium hydride / toluene; mineral oil / 2 h / 0 - 20 °C
1.2: Reflux
2.1: zinc(II) chloride / N,N-dimethyl-formamide / 3.5 h / 105 °C
3.1: caesium carbonate / 1-methyl-pyrrolidin-2-one / 0.33 h / 20 °C
3.2: 4 h / 80 °C
4.1: nitric acid / dichloromethane / 1.5 h / 0 - 20 °C
5.1: potassium phosphate / palladium diacetate; tert-butyl XPhos / toluene / 2 h / 100 °C / Inert atmosphere
6.1: boron trichloride / dichloromethane / -78 - -40 °C
7.1: triethylamine / dmap / dichloromethane / 1 h / 0 - 20 °C
8.1: sodium acetate / (diphenylphosphin)ferrocene; palladium diacetate / acetonitrile / 2 h / 100 °C / Inert atmosphere
9.1: hydrogenchloride; water / tetrahydrofuran / 1 h / Reflux
10.1: tin(II) chloride dihdyrate / ethyl acetate / 1 h / 80 °C
10.2: 20 °C / pH 8 - 9
11.1: pyridine / 2 h / 0 - 30 °C
12.1: sodium tetrahydroborate / tetrahydrofuran / 0.5 h / 0 °C
13.1: sodium hydride / dichloromethane; paraoil / 15 h / 0 - 20 °C
With
pyridine; hydrogenchloride; sodium tetrahydroborate; potassium phosphate; tin(II) chloride dihdyrate; water; nitric acid; sodium acetate; boron trichloride; sodium hydride; caesium carbonate; triethylamine; zinc(II) chloride;
dmap; (diphenylphosphin)ferrocene; palladium diacetate; tert-butyl XPhos;
In
tetrahydrofuran; 1-methyl-pyrrolidin-2-one; dichloromethane; paraoil; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile; mineral oil;