Multi-step reaction with 11 steps
1.1: N-Bromosuccinimide / tetrahydrofuran / 1 h / 20 - 25 °C
2.1: triethylamine / dichloromethane / 1 h / 0 - 20 °C
3.1: n-butyllithium / tetrahydrofuran / 0.33 h / -78 °C
3.2: 0.5 h / -78 °C
4.1: caesium carbonate / tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 4 h / 90 °C / Inert atmosphere
5.1: hydrogenchloride; water / methanol / 0.25 h / 50 °C
6.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 2 h / 20 °C
7.1: tetrabutyl ammonium fluoride / trifluoroacetic acid-d1 / 16 h / 20 °C
8.1: triethylamine / dichloromethane / 1 h / 0 - 20 °C
9.1: sodium azide / N,N-dimethyl-formamide / 16 h / 20 °C
10.1: triphenylphosphine / tetrahydrofuran / 2 h / 20 °C
10.2: 1 h / 80 °C
11.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 20 °C
With
hydrogenchloride; N-Bromosuccinimide; n-butyllithium; sodium azide; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; water; caesium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine;
tetrakis(triphenylphosphine) palladium(0);
In
tetrahydrofuran; methanol; dichloromethane; trifluoroacetic acid-d1; N,N-dimethyl-formamide;