HuagongsheHuagongshe Chemistry Print Report · For research reference only
Tetrahydrofuran → 5-Chloro-2-(pyridin-4-yl)-6-(trifluoromethyl)benzoxazole
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | ethyl N-ethoxycarbonyliminocarbamate | HCID 220568 | — |
| Reactant | N-[5-chloro-2-hydroxy-4-trifluoromethylphenyl]isonicotinamide | HCID 66879747 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | 5-Chloro-2-(pyridin-4-yl)-6-(trifluoromethyl)benzoxazole | HCID 66880218 | 21.2% |
Reaction Steps
To a mixture of 0.55 g of N-[5-chloro-2-hydroxy-4-(trifluoromethyl)phenyl]isonicotinamide, 6 ml of tetrahydrofuran and 0.50 g of triphenylphosphine, 0.83 g of 40% toluene solution of diethyl azodicarboxylate was added dropwise at room temperature. The reaction mixture was stirred for 1.5 hours. The reaction mixture was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography, and the resultant crystals were washed with methanol to give 0.11 g of 5-chloro-2-(pyridin-4-yl)-6-(trifluoromethyl)benzoxazole (hereinafter, referred to as “active compound 78”).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08445522B2 |
| Source dataset | uspto-grants-2013_05 |
| ORD ID | ord-87b439adc1da430d81d7ab67b699be7c |
| Source note | uspto-grants-2013_05 |