HuagongsheHuagongshe Chemistry Print Report · For research reference only
Potassium Carbonate → 2-Ethyl-6-(2-methoxy-4-trifluoromethoxy-phenyl)-5-methyl-3-nitro-pyridine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | Ethylboronic acid | HCID 521157 | — |
| Reactant | 2-Chloro-6-(2-methoxy-4-trifluoromethoxy-phenyl)-5-methyl-3-nitro-pyridine | HCID 22490059 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | 2-Ethyl-6-(2-methoxy-4-trifluoromethoxy-phenyl)-5-methyl-3-nitro-pyridine | HCID 21104788 | — |
Reaction Steps
Tetrakistriphenylphosphinepalladium(0) (0.03 g, 0.03 mmol) is added to 2-chloro-6-(2-methoxy-4-trifluoromethoxy-phenyl)-5-methyl-3-nitro-pyridine (0.10 g, 0.27 mmol) in toluene (5 mL). Ethyl boronic acid (0.1 g, 1.1 mmol) and potassium carbonate (0.07 g, 0.55 mmol)) are added to this solution, and the reaction is heated to reflux for 17 hours. The product is extracted with ethyl acetate (20 mL). Combined extracts are washed with brine (20 mL), dried over sodium sulfate, and concentrated in vacuo. Purification by flash column chromatography (5% EtOAC-hexane) yields 2-ethyl-6-(2-methoxy-4-trifluoromethoxy-phenyl)-5-methyl-3-nitro-pyridine as a yellow solid TLC Rf 0.55 (elution with 10% ethyl acetate-hexane)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07223778B2 |
| Source dataset | uspto-grants-2007_05 |
| ORD ID | ord-f5a6c076e3eb4efc86f2cd89bb2ad8f5 |
| Source note | uspto-grants-2007_05 |