HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium hydride → 4-(4-Amino-2,5-difluorophenoxy)pyridine-2-carboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | 4-Chloropyridine-2-carboxamide | HCID 303543 | — |
| Reactant | 4-Amino-2,5-difluorophenol | HCID 2778762 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 4-(4-Amino-2,5-difluorophenoxy)pyridine-2-carboxamide | HCID 24788628 | 30.6% |
Reaction Steps
To a mixture of 4-amino-2,5-difluorophenol (100 mg, 0.64 mmol), and 4-chloropicolinamide (110 mg, 0.71 mmol) in DMF (2 mL) was added NaH (80 mg, 1.3 mmol, 60% dispersed in mineral oil). The reaction mixture was microwaved at 120° C. for 1.5 hours, then cooled to rt, diluted with water (20 mL), and extracted with EtOAc (30 mL×3). The combined organic phases were washed with brine (80 mL), dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash column chromatography with (EtOAc/PE (v/v)=4/1) to afford the title compound as a brown solid (52 mg, 26%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09326975B2 |
| Source dataset | uspto-grants-2016_05 |
| ORD ID | ord-22856af2919440daad49437f93317de0 |
| Source note | uspto-grants-2016_05 |