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-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-4-fluoro-6-(1-oxo-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-2(1H)-yl)benzyl Acetate | HCID 58044205 | — |
| Reactant | HCID 86684128 | HCID 86684128 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 86684129 | HCID 86684129 | 60.3% |
Reaction Steps
A 250-mL single-neck round-bottomed flask equipped with a magnetic stirrer and reflux condenser was charged with 1,4-dioxane (60 mL), 106c (200 mg, 0.5 mmol), 4-fluoro-2-(1-oxo-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-2(1H)-yl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl acetate 101l (385 mg, 0.8 mmol), and cesium carbonate (332 mg, 1 mmol). Xantphos (30 mg, 0.08 mmol) and Pd2(dba)3 (55 mg, 0.08 mmol) were added, and the reaction mixture was heated at 90° C. for 4 h. After this time the reaction was cooled to room temperature, it was filtered and the filtrate was concentrated under reduced pressure. The residue was purified on flash column eluting with CH2Cl2/MeOH (10:1) to afford 106d (200 mg, 60%). MS: [M+H]+ 664.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08722676B2 |
|---|
| Source dataset | uspto-grants-2014_05 |
|---|
| ORD ID | ord-c5da729f696a4b37b10ddac905b9d2ea |
|---|
| Source note | uspto-grants-2014_05 |
|---|
