Multi-step reaction with 10 steps
1.1: 1H-imidazole / dichloromethane / 2.67 h / 10 - 20 °C
2.1: n-butyllithium / tetrahydrofuran; water / 4 h / -73 - -70 °C
2.2: 1.08 h / -73 - -70 °C
3.1: n-butyllithium / tetrahydrofuran / 1.75 h / -75 - -70 °C
3.2: 3 h / -75 - -70 °C
4.1: hydrogen / palladium 10% on activated carbon / acetic acid; ethyl acetate / 3 h / 20 °C
5.1: tetraethylammonium fluoride / tetrahydrofuran / 1 h / 20 °C
5.2: 0.25 h
6.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 20 °C
6.2: 16 h / 0 - 20 °C
7.1: trimethylsilyl bromide / dichloromethane / 16 h / 0 - 20 °C
8.1: water / acetonitrile / 16 h / 0 - 20 °C
9.1: oxalyl dichloride / N,N-dimethyl-formamide / 1,2-dimethoxyethane / 3 h / 20 - 50 °C
10.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 14 h / 0 - 20 °C
With
1H-imidazole; n-butyllithium; oxalyl dichloride; trimethylsilyl bromide; water; hydrogen; sodium hydride; tetraethylammonium fluoride; N-ethyl-N,N-diisopropylamine;
palladium 10% on activated carbon; N,N-dimethyl-formamide;
In
tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; water; acetic acid; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;