Water → HCID 58305685, compound

HRID 1851327Notes

Reaction equation

HRID 1851327 reaction equation
C1C(=O)N([Br:8])C(=O)C1.[C:9]([C:11]1[CH:16]=[CH:15][C:14]([N:17]2[CH:21]=[CH:20][CH:19]=[C:18]2[CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])=[C:13]([CH3:29])[CH:12]=1)#[N:10].O>CN(C=O)C>[Br:8][C:21]1[N:17]([C:14]2[CH:15]=[CH:16][C:11]([C:9]#[N:10])=[CH:12][C:13]=2[CH3:29])[C:18]([CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 58305666HCID 58305666, compound

Product 1

HCID 58305685HCID 58305685, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

NBS (4.76 g, 1 equiv) was added portionwise to a solution of ethyl 3-(1-(4-cyano-2-methylphenyl)-1H-pyrrol-2-yl)propanoate in DMF at 0° C. during 45 min. After addition, the mixture was stirred at room temperature for 30 min, then poured into water, and extracted with ethyl acetate for three times. The combined organic layers were washed with brine, dried over Na2SO4, concentrated and purified by silica gel column chromatography (PE:EA=15:1) to afford ethyl 3-(5-bromo-1-(4-cyano-2-methylphenyl)-1H-pyrrol-2-yl)propanoate as a white solid.

Workup

  1. additionAfter addition
  2. extractionextracted with ethyl acetate for three times
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. custompurified by silica gel column chromatography (PE:EA=15:1)

Sources & evidence

ORD record
ord-b3b1639008a14ae3bb3742a9ee2699eb
Source dataset
uspto-grants-2015_02
Patent number
US08957105B2

Reaction notes

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