Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Pyridine | HCID 1049 | — |
| Reactant | 4-Bromobenzoyl chloride | HCID 68515 | — |
| Reactant | Methyl 3-(methylamino)but-2-enoate | HCID 2734182 | — |
| Reactant | Pyridinium chloride | HCID 10176127 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 178483595 | HCID 178483595 | — |
Reaction Steps
4-Bromobenzoyl chloride (17.14 g, 78.1 mmol) and 3-methylamino-but-2-enoic acid methyl ester (10.0 g, 78.1 mmol) were combined in THF (600 mL) and cooled to 0° C. Pyridine (6.8 mL, 85.9 mmol) was added by syringe, and the reaction was stirred overnight at room temperature. Solid pyridine hydrochloride was observed on the flask walls, so the solution was decanted and then concentrated to 10% of its original volume. The residue was diluted with EtOAc (400 mL) and washed twice with H2O. The organic layer was dried, filtered, and concentrated to give the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08455499B2 |
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| Source dataset | uspto-grants-2013_06 |
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| ORD ID | ord-723ae594617645b3badbab679ce8d4ef |
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| Source note | uspto-grants-2013_06 |
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