Multi-step reaction with 12 steps
1.1: pyridine / dichloromethane / 0.5 h / 0 - 20 °C
2.1: potassium carbonate / N,N-dimethyl-formamide / 4 h / 80 °C
3.1: triethylamine; lithium chloride / palladium diacetate; triphenylphosphine / N,N-dimethyl-formamide / 1.5 h / 120 °C / Inert atmosphere
4.1: diethylzinc / hexane; toluene / 0 - 20 °C
5.1: N-Bromosuccinimide / dichloromethane / 24 h / 0 - 20 °C
6.1: boron tribromide / dichloromethane / 0.33 h / 0 °C
6.2: Cooling with ice
7.1: triethylamine / dmap / tetrahydrofuran / 1.5 h / 0 - 20 °C
8.1: piperidine / bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; tri-tert-butyl phosphine / N,N-dimethyl-formamide / 80 °C / Inert atmosphere
9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / Inert atmosphere; Reflux
10.1: N-iodo-succinimide / chloroform; trifluoroacetic acid / 3 h / 20 °C
11.1: triethylamine / tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 4 h / 60 °C
12.1: lithium hydroxide / tetrahydrofuran; methanol / 70 °C
12.2: 0 °C
With
piperidine; pyridine; N-Bromosuccinimide; N-iodo-succinimide; tetrabutyl ammonium fluoride; diethylzinc; boron tribromide; potassium carbonate; triethylamine; lithium chloride; lithium hydroxide;
dmap; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); tri-tert-butyl phosphine; palladium diacetate; triphenylphosphine;
In
tetrahydrofuran; methanol; hexane; dichloromethane; chloroform; N,N-dimethyl-formamide; toluene; trifluoroacetic acid;