HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cesium carbonate → 3-((3-Methyloxetan-3-yl)methoxy)-5-(4-(trifluoromethoxy)phenyl)benzo[d]isoxazole
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 1,2-Benzisoxazole | HCID 71073 | — |
| Reactant | Oxetane, 3-(bromomethyl)-3-methyl- | HCID 144860 | — |
| Reactant | HCID 178518982 | HCID 178518982 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 3-((3-Methyloxetan-3-yl)methoxy)-5-(4-(trifluoromethoxy)phenyl)benzo[d]isoxazole | HCID 118161932 | 61.8% |
Reaction Steps
5-(4-(trifluoromethoxy)phenyl)benzo[d]isoxazol-3-ol (100 mg, 0.34 mmol), 3-bromomethyl-3-methyloxetane (150 mg, 0.91 mmol) and cesium carbonate (300 mg) were combined in 5 mL DMF and stirred at ambient temperature until HPLC showed complete disappearance of benzisoxazole starting material. The reaction mixture was diluted with 60 mL ethyl acetate, washed with water and brine and evaporated under vacuum. Flash chromatographic purification on 12 g silica gel with 0-60% ethyl acetate in hexane gave the title compound (80 mg, 0.21 mmol).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09416115B2 |
| Source dataset | uspto-grants-2016_08 |
| ORD ID | ord-d95816126c8f44769fde3c0ae3d6ab27 |
| Source note | uspto-grants-2016_08 |