HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 393810Erstellt: 24. Oktober 2026
Cesium carbonate → benzyl (1S,5S)-6-(5-cyano-3-pyridinyl)-3,6-diazabicyclo[3.2.0]heptane-3-carboxylate
https://huagongshe.com/de/reaction/393810
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|
| Edukt | Cesium carbonate | HCID 10796 | — |
| Edukt | 5-Bromonicotinonitrile | HCID 736793 | — |
| Edukt | benzyl (1S,5S)-3,6-diazabicyclo[3.2.0]heptane-3-carboxylate | HCID 23635906 | — |
| Katalysator | Binap, (A+-)- | HCID 634876 | — |
| Katalysator | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Lösungsmittel | Toluene | HCID 1140 | — |
| Produkt | benzyl (1S,5S)-6-(5-cyano-3-pyridinyl)-3,6-diazabicyclo[3.2.0]heptane-3-carboxylate | HCID 23635910 | 47% |
Reaktionsschritte
The product of Example 52D (0.800 g, 3.40 mmol) in toluene (34 mL) was treated with 3-cyano-5-bromopyridine (0.690 g, 3.8 mmol), Pd2(dba)3 (0.0.64 g, 0.10 mmol), BINAP (0.086 g, 0.010 mmol) and Cs2CO3 (0.221 g, 6.80 mmol) and the reaction was heated at 80° C. for 12 hours. The mixture was allowed to cool to room temperature and then concentrated under reduced pressure. The residue was purified by chromatography (SiO2, 5% MeOH/CH2Cl2) to provide the title compound as a yellow oil (47%, 0.530 g). MS (DCI/NH3) m/z 335 (M+H)+.
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patentnummer | US06809105B2 |
|---|
| Quelldatensatz | uspto-grants-2004_10 |
|---|
| ORD ID | ord-7d9ac28f9b174eaa90991702dff29883 |
|---|
| Quellennotiz | uspto-grants-2004_10 |
|---|