Multi-step reaction with 12 steps
1.1: tert-butyl alcohol / 20 h / 60 °C
2.1: caesium carbonate / N,N-dimethyl-formamide / 4 h / 20 °C
3.1: hydrogen / palladium 10% on activated carbon / methanol / 19 h / 20 °C
4.1: tetrahydrofuran / 0.67 h / 0 °C
5.1: trifluoroacetic acid / 1 h / 0 °C
6.1: N,N-dimethyl-formamide / 23 h / 120 °C
7.1: hydrogen / palladium 10% on activated carbon / ethanol; tetrahydrofuran / 3 h / 20 °C
8.1: acetic acid / 0.33 h / 20 °C
8.2: 0.33 h / 20 °C
9.1: bromine; acetic acid / 16 h / 20 °C
10.1: pyridine / 2 h / -20 °C
11.1: sodium hydroxide; water / tetrahydrofuran; methanol / 19 h / 20 °C
12.1: N,N-dimethyl-formamide / 1 h / 20 °C
With
pyridine; water; hydrogen; bromine; caesium carbonate; acetic acid; trifluoroacetic acid; sodium hydroxide;
palladium 10% on activated carbon;
In
tetrahydrofuran; methanol; ethanol; N,N-dimethyl-formamide; tert-butyl alcohol;