Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 2-Bromo-6-fluoropyridine | HCID 639438 | — |
| Reactant | 4-Aminomethyltetrahydropyran | HCID 2773210 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 58127218 | HCID 58127218 | — |
Reaction Steps
To a solution of 2-bromo-6-fluoropyridine (3 g, 17.05 mmol) in DMSO (8 mL) was added (tetrahydro-2H-pyran-4-yl)methanamine (3.10 g, 20.46 mmol) and triethylamine (5.68 mL, 40.9 mmol). The mixture was heated at 110° C. for 18 hr. The mixture was allowed to cool to ambient temperature and diluted with EtOAc. The organic layer was washed with saturated aqueous NaHCO3 solution (1×), water (1×), brine (1×), dried over Na2SO4, filtered off and concentrated in vacuo. The resulting residue was purified by column chromatography over silica gel providing 6-bromo-N-((tetrahydro-2H-pyran-4-yl)methyl)pyridin-2-amine as a white solid. Yield: 4.24 g. LCMS (m/z): 270.9/273.0 [M+H]+; Retention time=0.78 min.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08778951B2 |
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| Source dataset | uspto-grants-2014_07 |
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| ORD ID | ord-17de5971f0a64997a92e60850a5bbba0 |
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| Source note | uspto-grants-2014_07 |
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