HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methylboronic Acid → 3-{4-[4-(4-Methylbenzoyl)piperidine-1-carbonyl]phenyl}oxazolidin-2-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methylboronic Acid | HCID 139377 | — |
| Reactant | Potassium Fluoride | HCID 522689 | — |
| Reactant | 2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl | HCID 11269872 | — |
| Reactant | 3-{4-[4-(4-Chlorobenzoyl)piperidine-1-carbonyl]phenyl}oxazolidin-2-one | HCID 67380914 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 3-{4-[4-(4-Methylbenzoyl)piperidine-1-carbonyl]phenyl}oxazolidin-2-one | HCID 67380847 | 28.5% |
Reaction Steps
To a mixture of 3-{4-[4-(4-chlorobenzoyl)piperidine-1-carbonyl]phenyl}oxazolidin-2-one (413 mg) described in Example 40, methylboronic acid (120 mg), palladium (II) acetate (11 mg), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (41 mg) and potassium fluoride (232 mg) was added tetrahydrofuran (3 mL), and the mixture was refluxed for 5 hr. After cooling, water was added to the reaction mixture, and the mixture was extracted with chloroform. The organic layer was washed with saturated brine, and the solvent was evaporated. The residue was purified by column chromatography (chloroform:methanol) to give the title compound (112 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08354401B2 |
| Source dataset | uspto-grants-2013_01 |
| ORD ID | ord-c407703406ae45d199044f2f65f5cb32 |
| Source note | uspto-grants-2013_01 |