Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | N,N-Dimethylpropargylamine | HCID 81643 | — |
| Reactant | 2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl | HCID 11155794 | — |
| Reactant | 5-Bromo-2-fluoropyridin-3-amine | HCID 17750144 | — |
| Catalyst | Bis(acetonitrile)dichloropalladium | HCID 6093782 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 58476654 | HCID 58476654 | 45.4% |
Reaction Steps
A mixture of 5-bromo-2-fluoropyridin-3-amine (1.00 g, 5.24 mmol), N,N-dimethylprop-2-yn-1-amine (0.68 mL, 6.28 mmol), and cesium carbonate (3.41 g, 10.5 mmol) in DMF (25 mL) was degassed with argon for 15 min. To this slurry were added bis(acetonitrile)palladium(II)chloride (0.068 g, 0.26 mmol) and Xphos (0.324 g, 0.68 mmol). The suspension was allowed to stir at 50° C. for 4 h under an atmosphere of nitrogen and was then concentrated. The residue was purified by column chromatography to give 5-[3-(dimethylamino)prop-1-yn-1-yl]-2-fluoropyridin-3-amine (0.46 g, 45%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07998952B2 |
|---|
| Source dataset | uspto-grants-2011_08 |
|---|
| ORD ID | ord-4643883562864a579a473b2f11219f84 |
|---|
| Source note | uspto-grants-2011_08 |
|---|
