HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → N1-(2-Fluoroethyl)-5-[(2-amino-4-pyridyl)oxy]-1H-1-indolecarboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | 4-(1H-5-indolyloxy)-2-pyridinamine | HCID 21949365 | — |
| Reactant | Phenyl (2-fluoroethyl)carbamate | HCID 22936733 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | N1-(2-Fluoroethyl)-5-[(2-amino-4-pyridyl)oxy]-1H-1-indolecarboxamide | HCID 58931263 | 69.2% |
Reaction Steps
Sodium hydride (60% in oil) (360 mg) was added to a solution of 2.0 g of 5-[(2-amino-4-pyridyl)oxy]-1H-indole in 30 ml of dimethylformamide at room temperature. After stirring for 5 minutes, the mixture was placed in an ice bath and 1.8 g of phenyl N-(2-fluoroethyl)carbamate was added while cooling. The mixture was returned to room temperature and stirred for 30 minutes, after which water was added and extraction was performed with ethyl acetate. The extract was passed through a glass filter coated with silica gel. The ethyl acetate layer was washed once with bicarbonate water and dried over magnesium sulfate. The drying agent was filtered off to obtain 1.93 g of a faint brown powder.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08372981B2 |
| Source dataset | uspto-grants-2013_02 |
| ORD ID | ord-7a3e94728f08414ebf5d15a3f9d79058 |
| Source note | uspto-grants-2013_02 |