Multi-step reaction with 8 steps
1.1: potassium carbonate / acetonitrile / 6 h / 20 °C / Inert atmosphere
2.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere
2.2: 17 h / -78 - 20 °C / Inert atmosphere
3.1: palladium 10% on activated carbon; hydrogen / methanol / 3 h
4.1: 4-methyl-1,2,3-trifluorobenzene / 1 h / 120 °C / Microwave irradiation; Inert atmosphere
5.1: pyridine / dichloromethane / 2 h / 20 °C / Inert atmosphere
6.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / ethanol; water; toluene / 4 h / 80 °C / Inert atmosphere
7.1: water; sodium hydroxide / tetrahydrofuran; methanol / 0.17 h / 100 °C / Microwave irradiation; Inert atmosphere
8.1: carbon dioxide / methanol; isopropyl alcohol / 75007.5 Torr / Resolution of racemate; Inert atmosphere
With
pyridine; tetrakis(triphenylphosphine) palladium(0); carbon dioxide; palladium 10% on activated carbon; water; hydrogen; sodium carbonate; potassium carbonate; sodium hydroxide; lithium hexamethyldisilazane;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; water; isopropyl alcohol; toluene; acetonitrile; 4-methyl-1,2,3-trifluorobenzene;
4.1: Mannich reaction / 6.1: Suzuki coupling;
DOI:10.1021/ml200175q