HuagongsheHuagongshe Chemistry Print Report · For research reference only
Potassium Carbonate → Tert-butyl{4-chloro-2-fluoro-5-[(5-nitropyridin-2-yl)oxy]phenyl}carbamate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | 2-Chloro-5-nitropyridine | HCID 78308 | — |
| Reactant | tert-butyl N-(4-chloro-2-fluoro-5-hydroxyphenyl)carbamate | HCID 91597094 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | Tert-butyl{4-chloro-2-fluoro-5-[(5-nitropyridin-2-yl)oxy]phenyl}carbamate | HCID 91123393 | 46% |
Reaction Steps
A mixture of tert-butyl(4-chloro-2-fluoro-5-hydroxyphenyl)carbamate (6.70 g, 25.6 mmol), 2-chloro-5-nitropyridine (4.06 g, 25.6 mmol), potassium carbonate (3.89 g, 28.1 mmol) and N,N-dimethylformamide (70 mL) was stirred at room temperature for 30 min. To the reaction mixture was added aqueous ammonium chloride solution (100 mL), and the mixture was extracted with ethyl acetate (150 mL×3). The organic layers were combined, washed successively with water (100 mL) and saturated brine (50 mL), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give the title compound (4.52 g, 46%) as a white powder.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08344135B2 |
| Source dataset | uspto-grants-2013_01 |
| ORD ID | ord-59336fb066a447a2acec6d24acd27464 |
| Source note | uspto-grants-2013_01 |