Multi-step reaction with 9 steps
1.1: sodium hydroxide / toluene / 1 h
2.1: toluene-4-sulfonic acid / toluene / 16 h / Reflux; Water separator
3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.33 h / 0 °C
3.2: 12 h / 20 °C
4.1: sodium hydroxide; methanol / 3 h / 20 °C
4.2: pH 2
5.1: triethylamine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / ethyl acetate; tetrahydrofuran / 0.75 h / 0 °C / Inert atmosphere
5.2: 2.5 h / 20 °C
6.1: caesium carbonate / palladium diacetate; XPhos / water; tetrahydrofuran / 12 h / 80 °C / Inert atmosphere
7.1: hydrogenchloride; isopropyl alcohol / 12 h / 20 °C
7.2: pH 9
8.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 0 - 20 °C
9.1: potassium carbonate / N,N-dimethyl-formamide / 12 h / 20 °C
With
hydrogenchloride; methanol; sodium hydride; potassium carbonate; caesium carbonate; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine; N-ethyl-N,N-diisopropylamine; isopropyl alcohol; sodium hydroxide;
palladium diacetate; toluene-4-sulfonic acid; XPhos;
In
tetrahydrofuran; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; toluene; mineral oil;