HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cesium carbonate → N-{4-[5-(2-chlorophenyl)-4-(4-{[2-(trimethylsilyl)ethoxy]methyl}-4H-1,2,4-triazol-3-yl)-1,3-oxazol-2-yl]phenyl}acetamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 4-Acetamidophenylboronic acid | HCID 2734657 | — |
| Reactant | 3-[5-(2-chlorophenyl)-2-iodo-1,3-oxazol-4-yl]-4-{[2-(trimethylsilyl)-ethoxy]methyl}-4H-1,2,4-triazole | HCID 66749496 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | N-{4-[5-(2-chlorophenyl)-4-(4-{[2-(trimethylsilyl)ethoxy]methyl}-4H-1,2,4-triazol-3-yl)-1,3-oxazol-2-yl]phenyl}acetamide | HCID 66749648 | 91% |
Reaction Steps
A mixture of 3-[5-(2-chlorophenyl)-2-iodo-1,3-oxazol-4-yl]-4-{[2-(trimethylsilyl)-ethoxy]methyl}-4H-1,2,4-triazole (0.11 g, 0.22 mmol), tetrakis(triphenylphosphine)palladium(0) (0.050 g, 0.043 mmol), (4-acetamidophenyl)boronic acid (0.115 g, 0.64 mmol) and cesium carbonate (0.46 g, 1.40 mmol) in 1,4-dioxane (2 mL) and water (0.2 mL) was sealed in a tube and subjected to microwave irradiation at 150° C. for 60 min. The reaction mixture was concentrated and the residue was purified by column chromatography to give N-{4-[5-(2-chlorophenyl)-4-(4-{[2-(trimethylsilyl)ethoxy]methyl}-4H-1,2,4-triazol-3-yl)-1,3-oxazol-2-yl]phenyl}acetamide (0.100 g, 91%). LCMS (AA): m/z=510 (M+H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08859768B2 |
| Source dataset | uspto-grants-2014_10 |
| ORD ID | ord-ffe59bc0b8434328b7f863fdc0919274 |
| Source note | uspto-grants-2014_10 |