Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethanethiol | HCID 6343 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | HCID 86720177 | HCID 86720177 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 86720178 | HCID 86720178 | 71.5% |
Reaction Steps
To a solution of ethyl 2-chloro-4-methyl-7-(trifluoromethyl)-1,5-naphthyridine-3-carboxylate (0.97 g, 3.05 mmol, 1 eq.) in DMF (10 ml) were added K2CO3 (1.26 g, 9.15 mmol, 3 eq.) and ethanethiol (0.66 ml, 9.15 mmol, 3 eq.) at RT. The mixture was stirred at 60° C. for 16 h. Afterwards the mixture was diluted with water (80 ml) and was extracted with EtOAc (3×80 ml). The combined organic layers were washed with water (100 ml), brine (100 ml), dried over anhydrous Na2SO4 and evaporated to provide the crude product, which is purified by CC (EtOAc/hexane 1:9) to yield ethyl 2-(ethylthio)-4-methyl-7-(trifluoromethyl)-1,5-naphthyridine-3-carboxylate (0.75 g, 2.18 mmol, 71%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09248122B2 |
|---|
| Source dataset | uspto-grants-2016_02 |
|---|
| ORD ID | ord-efb864053e954aaab39a24913f2384a8 |
|---|
| Source note | uspto-grants-2016_02 |
|---|