Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium fluoride | HCID 25953 | — |
| Reactant | Stannane, tributyl(1-ethoxyethenyl)- | HCID 619414 | — |
| Reactant | 2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl | HCID 11155794 | — |
| Reactant | HCID 89782295 | HCID 89782295 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 89781962 | HCID 89781962 | 78% |
Reaction Steps
A mixture of 8-chloro-N-phenylquinoxalin-2-amine (0.65 g, 2.54 mmol), tributyl(1-ethoxyvinyl)stannane (1.288 ml, 3.81 mmol, Aldrich), Pd2(dba)3 (0.582 g, 0.636 mmol), XPhos (Strem, Newburyport, Mass.; 0.303 g, 0.636 mmol), copper(I) iodide (0.097 g, 0.508 mmol), and cesium fluoride (0.772 g, 5.08 mmol) in dioxane (12.71 ml) was heated in a microwave (Biotage Initiator) for 20 min at 160° C. Purification by silica gel (100% hexanes to 30% EtOAc/hexanes) provided 1-(3-(phenylamino)quinoxalin-5-yl)ethanone (180b, 78% yield) as a yellow oil. MS (ESI, pos. ion) m/z: 264.2 (M+1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09394297B2 |
|---|
| Source dataset | uspto-grants-2016_07 |
|---|
| ORD ID | ord-4e5e0f9ddf27428c9c008e7f20b42f3a |
|---|
| Source note | uspto-grants-2016_07 |
|---|
