Pyridine → HCID 178483595, compound

HRID 1253762Notes

Reaction equation

HRID 1253762 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[CH3:11][O:12][C:13](=[O:19])[CH:14]=[C:15]([NH:17][CH3:18])[CH3:16].N1C=CC=CC=1.Cl.N1C=CC=CC=1>C1COCC1>[CH3:11][O:12][C:13](=[O:19])[CH:14]([C:6](=[O:7])[C:5]1[CH:9]=[CH:10][C:2]([Br:1])=[CH:3][CH:4]=1)/[C:15](=[N:17]/[CH3:18])/[CH3:16]

Participants

6

Reactant 4

HCID 1049PyridineHCID 685154-Bromobenzoyl chlorideHCID 2734182Methyl 3-(methylamino)but-2-enoateHCID 10176127Pyridinium chloride

Product 1

HCID 178483595HCID 178483595, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

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.

Workup

  1. customwas decanted
  2. concentrationconcentrated to 10% of its original volume
  3. additionThe residue was diluted with EtOAc (400 mL)
  4. washwashed twice with H2O
  5. customThe organic layer was dried
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-723ae594617645b3badbab679ce8d4ef
Source dataset
uspto-grants-2013_06
Patent number
US08455499B2

Reaction notes

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