HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cesium carbonate → HCID 59532375, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 4-Fluorophenylboronic acid | HCID 285645 | — |
| Reactant | HCID 59532386 | HCID 59532386 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 59532375 | HCID 59532375 | 73% |
Reaction Steps
Pd(PPh3)2Cl2 (100 mg) was added to the solution of (R)-6-allyl-3-((S)-1-(4-bromophenyl)ethyl)-6-(thiophen-2-yl)-1,3-oxazinan-2-one (1.0 g, 2.5 mmol), 4-fluorophenylboronic acid (420 mg, 3.0 mmol) in 1,4-dioxane. Cs2CO3 (5 mL) was slowly added. The mixture was heated to reflux for 2 h. The mixture was quenched with water and separated, extracted with EtOAc twice, dried over anhydrous Na2SO4 and concentrated to afford the residue, which was purified by TLC to give (R)-6-allyl-3-((S)-1-(4′-fluorobiphenyl-4-yl)ethyl)-6-(thiophen-2-yl)-1,3-oxazinan-2-one (768 mg, 73%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08487094B2 |
| Source dataset | uspto-grants-2013_07 |
| ORD ID | ord-e3ed83bce9794956aa7af4997458c97e |
| Source note | uspto-grants-2013_07 |