Sodium hydride → HCID 57423710, compound

HRID 1725173Notes

Reaction equation

HRID 1725173 reaction equation
[CH2:1]([C:8]1[NH:9][C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:11][CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:22][C:23]([O:25][CH3:26])=[O:24]>CN(C=O)C>[CH3:26][O:25][C:23](=[O:24])[CH2:22][N:9]1[C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:11][CH:12]=[C:8]1[CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 57423709HCID 57423709, compound

Product 1

HCID 57423710HCID 57423710, compoundYield 39.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-benzyl-5-phenyl-1H-pyrrole (467 mg, 2.0 mmo) in DMF (5 ml) was added NaH (60% in mineral oil, 240 mg, 6.0 mmol) at room temperature in one portion. After stirring for 30 min at room temperature, the reaction mixture was heated to 60° C. and methyl bromoacetate (0.57 ml, 6.0 mmol) was added. After 1 h stirring at 60° C., the reaction was cooled and quenched with aqueous 1N HCl (30 ml). The aqueous was extracted with EtOAc (3×30 ml). The combined organic extracts were washed with aqueous 1N HCl (30 ml), H2O (30 ml), brine (30 ml), dried (MgSO4) and concentrated. The crude material was purified by chromatography (EtOAc/hexane: 3/97) to afford the titled compound (240 mg, 39%) as an oil: MS (+) ES, 306 (M+H)+.

Workup

  1. temperaturethe reaction mixture was heated to 60° C.
  2. stirringAfter 1 h stirring at 60° C.
  3. temperaturethe reaction was cooled
  4. customquenched with aqueous 1N HCl (30 ml)
  5. extractionThe aqueous was extracted with EtOAc (3×30 ml)
  6. washThe combined organic extracts were washed with aqueous 1N HCl (30 ml), H2O (30 ml), brine (30 ml)
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated
  9. customThe crude material was purified by chromatography (EtOAc/hexane: 3/97)

Sources & evidence

ORD record
ord-77b5ecdff46e41389ecec6a0c4fb72db
Source dataset
uspto-grants-2009_02
Patent number
US07488832B2

Reaction notes

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