Multi-step reaction with 10 steps
1.1: 19 h / 20 - 30 °C
2.1: triethylamine / dichloromethane / 72 h / 0 - 20 °C
3.1: palladium 10% on activated carbon; hydrogen / methanol / 2 h / 20 °C / 900.09 Torr
4.1: triphenylphosphine / N,N-dimethyl-formamide / 4 h / 135 °C
4.2: 0.5 h / 0 °C
5.1: borane-THF / tetrahydrofuran / 20 °C
6.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.17 h / 20 °C
6.2: 20 °C
7.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; carbon monoxide / methanol / 20 h / 100 °C / 52505.3 Torr
8.1: water / methanol; tetrahydrofuran; water / 20 °C
9.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; triethylamine / dichloromethane / 0.25 h / 20 °C
9.2: 4 h / 20 °C
10.1: water / methanol; tetrahydrofuran; water / 17 h / 20 °C
With
(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; borane-THF; carbon monoxide; palladium 10% on activated carbon; water; hydrogen; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate;
In
tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1002/cmdc.201200474