Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | Binap, (A+-)- | HCID 634876 | — |
| Reactant | 1-((Pyridin-4-yl)methyl)piperazine | HCID 808715 | — |
| Reactant | HCID 58368658 | HCID 58368658 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 58368496 | HCID 58368496 | 16% |
Reaction Steps
A stirred mixture of 7-acetyl-5-chloroquinolin-8-yl trifluoromethanesulfonate (0.12 g, 0.34 mmol, from Example 47, Step 2), 1-(pyridin-4-ylmethyl)piperazine (0.072 g, 0.41 mmol), palladium acetate (1.5 mg, 0.0067 mmol), (S)-(−)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (6.3 mg, 0.010 mmol), and cesium carbonate (0.31 g, 0.95 mmol) in tetrahydrofuran (3 mL) was heated at 65° C. overnight. The mixture was cooled, diluted with dichloromethane and filtered. The filtrate was washed with brine, dried over MgSO4 and evaporated. The resulting residue was purified on silica gel (eluting with 0 to 10% methanol in dichloromethane) to give the desired product (20.2 mg, 16%). LCMS calculated for C21H22ClN4O (M+H)+: m/z=381.1; Found: 381.1.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08680108B2 |
|---|
| Source dataset | uspto-grants-2014_03 |
|---|
| ORD ID | ord-ae319ebb484940e1bbeaa1195e76021d |
|---|
| Source note | uspto-grants-2014_03 |
|---|