Multi-step reaction with 8 steps
1.1: N-iodo-succinimide / palladium diacetate / N,N-dimethyl-formamide / 17 h / 100 °C
2.1: diazomethyl-trimethyl-silane / dichloromethane; diethyl ether / 0.75 h / 0 °C / Inert atmosphere
3.1: N-Bromosuccinimide / dibenzoyl peroxide / chlorobenzene / 18 h / 90 °C
3.2: 17 h
4.1: triethylamine / triphenylphosphine; copper(l) iodide; trans-bis(triphenylphosphine)palladium dichloride / N,N-dimethyl-formamide / 0.67 h / 100 °C / microwave irradiation
5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 °C / Inert atmosphere
6.1: triethylamine / triphenylphosphine; copper(l) iodide; trans-bis(triphenylphosphine)palladium dichloride / N,N-dimethyl-formamide / 0.33 h / 120 °C / Inert atmosphere; microwave irradiation
7.1: hydrogen / 10 wt% Pd(OH)2 on carbon / N,N-dimethyl-formamide / 18 h / 20 °C / Inert atmosphere
8.1: trifluoroacetic acid / dichloromethane / 2 h / 20 - 35 °C / Inert atmosphere
With
N-Bromosuccinimide; N-iodo-succinimide; tetrabutyl ammonium fluoride; hydrogen; triethylamine; trifluoroacetic acid; diazomethyl-trimethyl-silane;
copper(l) iodide; trans-bis(triphenylphosphine)palladium dichloride; 10 wt% Pd(OH)2 on carbon; palladium diacetate; triphenylphosphine; dibenzoyl peroxide;
In
tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; chlorobenzene;