Multi-step reaction with 14 steps
1.1: 1H-imidazole / N,N-dimethyl-formamide / 3 h / 20 °C / Cooling
2.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 20 h / 0 - 20 °C
2.2: 3 h / 0 - 20 °C
2.3: 3 h / -78 - 20 °C
3.1: n-butyllithium / tetrahydrofuran / 0.17 h / -78 °C
3.2: 0.83 h / -78 °C
4.1: thionyl chloride / pyridine / 2 h / 0 - 20 °C
5.1: hydrogen / palladium 10% on activated carbon / methanol / 3 h
6.1: N,N-dimethyl-formamide / 20 h / 95 °C
6.2: 2 h / 20 °C
7.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 20 °C
8.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -78 °C
9.1: toluene / 2 h / 110 °C
10.1: pyridine; acetic acid / acetonitrile / 1.5 h / 110 °C / Microwave irradiation
11.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 6 h / 20 °C
12.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran; toluene / 20 °C
13.1: boron trichloride / dichloromethane / 2 h / -78 °C
14.1: sulphamoyl chloride; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide; acetonitrile / 4 h / 0 - 20 °C
With
pyridine; 1H-imidazole; n-butyllithium; thionyl chloride; sulphamoyl chloride; tetrabutyl ammonium fluoride; hydrogen; boron trichloride; caesium carbonate; acetic acid; N-ethyl-N,N-diisopropylamine; 9-bora-bicyclo[3.3.1]nonane; triphenylphosphine; lithium diisopropyl amide; diethylazodicarboxylate;
palladium 10% on activated carbon;
In
tetrahydrofuran; pyridine; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;