Multi-step reaction with 11 steps
1.1: lithium hydroxide; water / tetrahydrofuran; methanol / 2 - 3 h / 90 °C / Heating / reflux
1.2: 1 h / 2 - 20 °C
2.1: silver carbonate / tetrahydrofuran; dichloromethane / 0 - 20 °C / Molecular sieve
3.1: sodium carbonate; lithium chloride / tetrakis(triphenylphosphine) palladium(0) / ethanol; water; toluene / 0.25 h
3.2: 4 h / 85 °C
4.1: caesium carbonate / N,N-dimethyl-formamide / 4 h / 65 °C
5.1: trifluoroacetic acid / dichloromethane / 2.5 h / 20 °C
6.1: 1,1'-carbonyldiimidazole / tetrahydrofuran / 1.5 h / 60 °C
6.2: 0.17 h / 20 °C
6.3: 3 h / 20 °C
7.1: sodium hydride / dimethyl sulfoxide / 0.5 h
7.2: 1 h
8.1: sodium hydroxide; water / tetrahydrofuran; methanol / 2 h / 60 °C
8.2: 20 °C
9.1: triethylamine; HATU / N,N-dimethyl-formamide / 1 h / 20 °C
10.1: hydrogen / palladium 10% on activated carbon / methanol; dichloromethane / 7 h / 2585.81 Torr
11.1: triethylamine; HATU / N,N-dimethyl-formamide / 1 h / 20 °C
With
lithium hydroxide; sodium hydroxide; water; hydrogen; sodium hydride; sodium carbonate; caesium carbonate; triethylamine; HATU; 1,1'-carbonyldiimidazole; silver carbonate; trifluoroacetic acid; lithium chloride;
tetrakis(triphenylphosphine) palladium(0); palladium 10% on activated carbon;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene;