Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethanol | HCID 702 | — |
| Reactant | Pyridine | HCID 1049 | — |
| Reactant | Pyrrolidine | HCID 31268 | — |
| Reactant | Ethyl bromopyruvate | HCID 66144 | — |
| Reactant | 2-Amino-6-bromo-3-pyridinecarboxaldehyde | HCID 72212598 | — |
| Product | HCID 86726878 | HCID 86726878 | — |
Reaction Steps
A solution of pyridine (0.13 mL, 1.6 mmol) and ethyl bromopyruvate (0.22 mL, 1.7 mmol) in EtOH (0.5 mL) was stirred at 70° C. in a sealed vial for 16 h. The reaction mixture was allowed to cool to ambient temperature and a solution of 2-amino-6-bromonicotinaldehyde (317 mg, 1.58 mmol) and pyridine (0.76 mL, 9.5 mmol) in EtOH (1 mL) was added. The reaction mixture then was heated at 100° C. in a sealed vial for 16 h. Pyrrolidine (0.26 mL, 3.2 mmol) was added, and stirring in the sealed vial was continued at 100° C. i for 16 h. The crude reaction mixture was purified by flash chromatography (40 g silica gel column, eluting with 0-100% EtOAc/hexanes) to afford the sub-title compound. LCMS (ESI) calc. for C13H16N3O3 [M+H]+: m/z=262.1. found: 262.0.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09278950B2 |
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| Source dataset | uspto-grants-2016_03 |
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| ORD ID | ord-0cc41acc01694846b84a176fd056cb2b |
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| Source note | uspto-grants-2016_03 |
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