HuagongsheHuagongshe Chemistry Print Report · For research reference only
Tetrahydrofuran → 6-Chloro-2-(3-fluoropyridin-4-yl)-5-(trifluoromethyl)benzoxazole
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | ethyl N-ethoxycarbonyliminocarbamate | HCID 220568 | — |
| Reactant | 3-fluoro-N-[4-chloro-2-hydroxy-5-trifluoromethylphenyl]isonicotinamide | HCID 66880048 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | 6-Chloro-2-(3-fluoropyridin-4-yl)-5-(trifluoromethyl)benzoxazole | HCID 66880110 | 88.4% |
Reaction Steps
To a mixture of 2.08 g of 3-fluoro-N-[4-chloro-2-hydroxy-5-(trifluoromethyl)phenyl]isonicotinamide, 13 ml of tetrahydrofuran and 1.79 g of triphenylphosphine, 2.98 g of 40% toluene solution of diethyl azodicarboxylate was added dropwise at room temperature. The reaction mixture was stirred for one hour. The reaction mixture was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 1.74 g of 6-chloro-2-(3-fluoropyridin-4-yl)-5-(trifluoromethyl)benzoxazole (hereinafter, referred to as “active compound 90”).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08609705B2 |
| Source dataset | uspto-grants-2013_12 |
| ORD ID | ord-65244a05612646e9821f2376f752c237 |
| Source note | uspto-grants-2013_12 |