HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Bicarbonate → tert-butyl {(1S)-2-[4-(6-ethoxy-3-fluoropyrazolo[1,5-a]pyridin-2-yl)phenoxy]-1-methylethyl}carbamate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | 1,1'-Difluoro-2,2'-bipyridinium Bis(tetrafluoroborate) | HCID 2733931 | — |
| Reactant | tert-butyl {(1S)-2-[4-(6-ethoxypyrazolo[1,5-a]pyridin-2-yl)phenoxy]-1-methylethyl}carbamate | HCID 86666306 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | tert-butyl {(1S)-2-[4-(6-ethoxy-3-fluoropyrazolo[1,5-a]pyridin-2-yl)phenoxy]-1-methylethyl}carbamate | HCID 86666308 | 30.9% |
Reaction Steps
A mixture of tert-butyl {(1S)-2-[4-(6-ethoxypyrazolo[1,5-a]pyridin-2-yl)phenoxy]-1-methylethyl}carbamate (400 mg), 1,1′-difluoro-2,2′-bipyridinium bis(tetrafluoroborate) (358 mg) and acetonitrile (3 mL) was stirred at room temperature for 3 hr. The reaction mixture was neutralized with saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The separated organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound as colorless crystals (129 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08729102B2 |
| Source dataset | uspto-grants-2014_05 |
| ORD ID | ord-f01fec0313724749acbdd72e49325091 |
| Source note | uspto-grants-2014_05 |