HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cesium carbonate → (S)-1-methyl-6-(4-((1-(pyridin-2-yl)pyrrolidin-3-yl)methoxy)-3-(trifluoromethyl)phenyl)-1H-[1,2,3]triazolo[4,5-c]pyridine-4-carbonitrile
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | Tetrabutylammonium | HCID 16028 | — |
| Reactant | (S)-(1-(pyridin-2-yl)pyrrolidin-3-yl)methyl methanesulfonate | HCID 86673348 | — |
| Reactant | 6-(4-hydroxy-3-(trifluoromethyl)-phenyl)-1-methyl-1H-[1,2,3]triazolo[4,5-c]pyridine-4-carbonitrile | HCID 136352311 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | (S)-1-methyl-6-(4-((1-(pyridin-2-yl)pyrrolidin-3-yl)methoxy)-3-(trifluoromethyl)phenyl)-1H-[1,2,3]triazolo[4,5-c]pyridine-4-carbonitrile | HCID 67298894 | — |
Reaction Steps
6-(4-Hydroxy-3-(trifluoromethyl)phenyl)-1-methyl-1H-[1,2,3]triazolo[4,5-c]pyridine-4-carbonitrile (0.313 mmol, 0.1 g), (S)-(1-(pyridin-2-yl)pyrrolidin-3-yl)methyl methanesulfonate (0.376 mmol, 0.096 g), cesium carbonate (0.470 mmol, 0.153 g) and tetrabutylammonium idodide (0.157 mmol, 0.058 g) were stirred in DMF (1 ml) at 50° C. overnight. The reaction mixture was diluted with ethyl acetate, washed with water and dried over Na2SO4. The resulting residue was triturated with ether and filtered. The solid was sonicated in methanol, filtered and dried to afford (S)-1-methyl-6-(4-((1-(pyridin-2-yl)pyrrolidin-3-yl)methoxy)-3-(trifluoromethyl)phenyl)-1H-[1,2,3]triazolo[4,5-c]pyridine-4-carbonitrile. (0.032 g)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09115126B2 |
| Source dataset | uspto-grants-2015_08 |
| ORD ID | ord-3b6da1c8162b459c928a4e3bb53e9cce |
| Source note | uspto-grants-2015_08 |