HuagongsheHuagongshe Chemistry Print Report · For research reference only
Tetrahydrofuran → 2-(3-Bromopyridin-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-bromo-N-[2-hydroxy-5-(trifluoromethyl)phenyl]isonicotinamide | HCID 66879880 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | 2-(3-Bromopyridin-4-yl)-5-(trifluoromethyl)benzoxazole | HCID 66880917 | 87.1% |
Reaction Conditions
| Temperature | 50 °C |
|---|
Reaction Steps
To a mixture of 0.29 g of 3-bromo-N-[2-hydroxy-5-(trifluoromethyl)phenyl]isonicotinamide, 4 ml of tetrahydrofuran and 0.25 g of triphenylphosphine, 0.42 g of 40% toluene solution of diethyl azodicarboxylate was added dropwise at room temperature. The reaction mixture was stirred while heating at 50° C. for 1.5 hours. The reaction mixture was cooled to room temperature, and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 0.24 g of 2-(3-bromopyridin-4-yl)-5-(trifluoromethyl)benzoxazole (hereinafter, referred to as “active compound 27”).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08609705B2 |
| Source dataset | uspto-grants-2013_12 |
| ORD ID | ord-5086dda980724981977988f9deade821 |
| Source note | uspto-grants-2013_12 |