HuagongsheHuagongshe Chemistry Print Report · For research reference only
Potassium Carbonate → 2-Fluoro-6-[(6-trifluoromethyl-pyridin-3-ylmethyl)-amino]-pyridine-3-carbaldehyde
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | Sodium Thiosulfate | HCID 24477 | — |
| Reactant | Triacetoxyperiodinane | HCID 159087 | — |
| Reactant | 2-Fluoro-6-[(6-trifluoromethyl-pyridin-3-ylmethyl)-amino]-pyridin-3-yl-methanol | HCID 57619300 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 2-Fluoro-6-[(6-trifluoromethyl-pyridin-3-ylmethyl)-amino]-pyridine-3-carbaldehyde | HCID 57619189 | 23.5% |
Reaction Steps
To 2-fluoro-6-[(6-trifluoromethyl-pyridin-3-ylmethyl)-amino]-pyridin-3-yl-methanol (563, 1.20 g, 3.98 mmol) in dichloromethane (40.0 mL) was added Dess-Martin periodinane (1.86 g, 4.38 mmol). The reaction was stirred at room temperature for 10 minutes, then poured into aqueous sodium thiosulfate and potassium carbonate, and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated and purified by silica gel column chromatography eluting with 20% to 100% ethyl acetate in hexane to give the desired compound (564, 0.28 g, 23.5%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09169250B2 |
| Source dataset | uspto-grants-2015_10 |
| ORD ID | ord-836d7b5bb25144de803eb76f0ba58c72 |
| Source note | uspto-grants-2015_10 |