Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Pyridine | HCID 1049 | — |
| Reactant | Acetic Anhydride | HCID 7918 | — |
| Reactant | 2,6-Dibromopyridin-4-amine | HCID 14091041 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 86680798 | HCID 86680798 | 94.3% |
Reaction Steps
To a solution of 2,6-dibromopyridin-4-amine (1.0 g, 3.97 mmol), DMAP (0.048 g, 0.397 mmol), and pyridine (0.482 mL, 5.95 mmol) in THF (7.94 mL) at rt was slowly added acetic anhydride (0.412 mL, 4.37 mmol), and the mixture was stirred at rt for 16 h, after which time the reaction was heated to 65° C. for a period of 5 days. After cooling to rt, MeOH (5 mL) was added and the reaction was concentrated under reduced pressure. The product was purified by silica gel chromatography using a gradient solvent system of 0-100% EtOAc/Hexanes. The product-containing fractions were collected and concentrated under reduced pressure to give N-(2,6-dibromopyridin-4-yl)acetamide (1.10 g, 94%) as a yellow solid. MS ESI calcd for C7H6Br2N2O [M+H]+ 293, found 293.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08796310B2 |
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| Source dataset | uspto-grants-2014_08 |
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| ORD ID | ord-44c43a32fe324c61972e5d25a5872e10 |
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| Source note | uspto-grants-2014_08 |
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