Multi-step reaction with 7 steps
1.1: palladium 10% on activated carbon; ammonium formate / methanol / 14 h / 20 °C
2.1: sodium hydrogencarbonate / water; 1,4-dioxane / 14 h / 0 - 20 °C
3.1: 6-chloro-3-((dimethylamino)(dimethyliminio)methyl)-1H-benzo[d][1,2,3]triazol-3-ium-1-olatehexafluorophosphate(V); N-ethyl-N,N-diisopropylamine / dichloromethane
4.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 0.17 h
5.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 4 h
6.1: tert.-butyl lithium / tetrahydrofuran; hexane / 1 h / -78 °C
6.2: 6 h / -20 °C
7.1: cerium(III) chloride heptahydrate; sodium tetrahydroborate / methanol / 0.08 h / 0 °C
With
sodium tetrahydroborate; 6-chloro-3-((dimethylamino)(dimethyliminio)methyl)-1H-benzo[d][1,2,3]triazol-3-ium-1-olatehexafluorophosphate(V); cerium(III) chloride heptahydrate; palladium 10% on activated carbon; tert.-butyl lithium; ammonium formate; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine;
In
tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; water;
DOI:10.1021/jm3016987