Multi-step reaction with 11 steps
1.1: caesium carbonate / N,N-dimethyl-formamide / 1 h / 80 °C
2.1: hydrogenchloride; water / acetonitrile / 0.5 h / 60 °C
3.1: ammonium chloride; zinc / tetrahydrofuran / 1 h
4.1: acetic acid / 1 h
4.2: pH 9
5.1: phenyllithium / tetrahydrofuran / -78 °C
5.2: 20 °C
6.1: hydrogen / palladium 10% on activated carbon / tetrahydrofuran; ethanol / 2585.81 Torr
7.1: boron dimethyl-trifluoro sulphide / acetonitrile / 0 - 20 °C
8.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0 - 20 °C
9.1: potassium carbonate / acetonitrile / 6 h / Reflux
10.1: water; lithium hydroxide / tetrahydrofuran / 2 h / 20 °C
10.2: pH ~ 6 - 7
11.1: ammonium chloride; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 1 h / 20 °C
With
hydrogenchloride; boron dimethyl-trifluoro sulphide; water; hydrogen; potassium carbonate; ammonium chloride; caesium carbonate; acetic acid; phenyllithium; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; lithium hydroxide; zinc;
palladium 10% on activated carbon;
In
tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;