HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cesium carbonate → Benzyl 4-(2-chloropyridin-4-yl)-3-oxo-2,4-diazabicyclo[3.1.0]hexane-2-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Reactant | 2-Chloro-4-iodopyridine | HCID 1516511 | — |
| Reactant | Benzyl 3-oxo-2,4-diazabicyclo[3.1.0]hexane-2-carboxylate | HCID 2802741 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | Benzyl 4-(2-chloropyridin-4-yl)-3-oxo-2,4-diazabicyclo[3.1.0]hexane-2-carboxylate | HCID 86729664 | 75% |
Reaction Steps
Using analogous reagents and reaction conditions as described in Example 1 above, benzyl 3-oxo-2,4-diazabicyclo[3.1.0]hexane-2-carboxylate (200 mg, 0.861 mmol) was reacted with 2-chloro-4-iodopyridine (227 mg, 0.947 mmol), xantphos (45 mg, 0.077 mmol), Pd2(dba)3 (24 mg, 0.025 mmol), cesium carbonate (421 mg, 1.29 mmol) and 1,4-dioxane (12 mL) at 100° C. for 3 hours. Purification by column chromatography on silica gel (50% ethyl acetate in hexane) afforded 220 mg of the product (75% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09029399B2 |
| Source dataset | uspto-grants-2015_05 |
| ORD ID | ord-d3f7667311524b91a37914c6abff7aba |
| Source note | uspto-grants-2015_05 |