Ethyl benzoylacetate → HCID 57659327, compound

HRID 2383000Notes

Reaction equation

HRID 2383000 reaction equation
Br.Br[CH2:3][C:4]([C:6]1[CH:11]=[CH:10][N:9]=[CH:8][CH:7]=1)=O.[CH2:12]([O:14][C:15](=[O:25])[CH2:16][C:17](=O)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH3:13].[H-].[Na+].C([O-])(=O)C.[NH4+:32]>C1COCC1>[CH2:12]([O:14][C:15]([C:16]1[CH:3]=[C:4]([C:6]2[CH:11]=[CH:10][N:9]=[CH:8][CH:7]=2)[NH:32][C:17]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:25])[CH3:13]

Participants

6

Reactant 4

HCID 7170Ethyl benzoylacetateHCID 24758Sodium hydrideHCID 517165Ammonium AcetateHCID 27762394-(Bromoacetyl)pyridine hydrobromide

Product 1

HCID 57659327HCID 57659327, compoundYield 60.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Bromo-1-pyridin-4-ylethanone hydrobromide 1 (1.7 g, 6.2 mmol) was added to a mixture of 3-oxo-3-phenyl-propionic acid ethyl ester 2 (R═H, 1 g, 5.2 mmol) in 100 mL of dry THF and NaH (0.5 g, 13.0 mmol) at 0° C. The solution was left at 0° C. for 1 h and then stirred at rt for 3 h. The solvent was removed and the residue was dissolved in 60 ml of EtOH, ammonium acetate (1.4 g, 18.7 mmol) was added and the reaction mixture was left overnight at rt. The crude material was purified by flash chromatography (DCM/MeOH 98:2) affording 920 mg (60%) of 2-phenyl-5-pyridin-4-yl-1H-pyrrole-3-carboxylic acid ethyl ester as a solid.

Workup

  1. customThe solvent was removed
  2. dissolutionthe residue was dissolved in 60 ml of EtOH
  3. waitthe reaction mixture was left overnight at rt
  4. customThe crude material was purified by flash chromatography (DCM/MeOH 98:2)

Sources & evidence

ORD record
ord-662c70f9e60a40cd8cd3207f1bc94d46
Source dataset
uspto-grants-2012_09
Patent number
US08263604B2

Reaction notes

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