Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 4-Aminotetrahydropyran | HCID 419223 | — |
| Reactant | 4-Bromo-2-fluoropyridine | HCID 2762851 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 86696663 | HCID 86696663 | 55.6% |
Reaction Steps
4-Bromo-2-fluoropyridine (1.38 g, 7.84 mmol) was dissolved in DMSO (20 mL), and (tetrahydro-pyran-4-yl)amine (0.912 g, 9.02 mmol) was added, followed by cesium carbonate (5.11 g, 15.7 mmol). The mixture was heated to 90° C. and agitated 3 hours. After cooling, the mixture was diluted with ethyl acetate (200 mL) and washed with water (5×), brine, dried and evaporated to give 4-bromo-N-(tetrahydro-2H-pyran-4-yl)pyridin-2-amine (1.12 g, 4.36 mmol, 55.5% yield) as an oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08697715B2 |
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| Source dataset | uspto-grants-2014_04 |
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| ORD ID | ord-ce28222cf5364c50a372ee75bbec49b3 |
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| Source note | uspto-grants-2014_04 |
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