HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Thiosulfate → HCID 178520051, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Thiosulfate | HCID 24477 | — |
| Reactant | Triacetoxyperiodinane | HCID 159087 | — |
| Reactant | cyclopropyl(1H-pyrazolo[3,4-b]pyridin-3-yl)methanol | HCID 178520052 | — |
| Solvent | Bicarbonate Ion | HCID 769 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 178520051 | HCID 178520051 | 50.5% |
Reaction Steps
Cyclopropyl(1H-pyrazolo[3,4-b]pyridin-3-yl)methanol (200 mg, 1.06 mmol) was taken up in DCM (8 mL). Dess-Martin (0.448 g, 1.06 mmol) was added to this solution, which was stirred at room temperature for 10 minutes. A solution of 10% sodium thiosulfate in saturated aqueous bicarbonate was added and resulted in a biphasic solution, which was vigorously stirred for 30 minutes. The organic layers were extracted with DCM (3×10 mL), dried over sodium sulfate and concentrated. Chromatography (EtOAc) afforded cyclopropyl(1H-pyrazolo[3,4-b]pyridin-3-yl)methanone (100 mg, 50.5%) as an oil, which crystallized upon standing.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08394795B2 |
| Source dataset | uspto-grants-2013_03 |
| ORD ID | ord-80856d4f76304506a8e205b906e91963 |
| Source note | uspto-grants-2013_03 |