5-(4-bromo-but-1-enyl)-3-methyl-1H-pyrrole-2,4-dicarboxylic acid 2-tert-butyl ester 4-ethyl ester → 2-O-tert-butyl 4-O-ethyl 5-(4-bromobutyl)-3-methyl-1H-pyrrole-2,4-dicarboxylate

HRID 2191497Notes

Reaction equation

HRID 2191497 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH3:23])=[C:8]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[NH:9][C:10]=1[CH:11]=[CH:12][CH2:13][CH2:14][Br:15])=[O:5])[CH3:2]>C(O)C.[Pd]>[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH3:23])=[C:8]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[NH:9][C:10]=1[CH2:11][CH2:12][CH2:13][CH2:14][Br:15])=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 685244215-(4-bromo-but-1-enyl)-3-methyl-1H-pyrrole-2,4-dicarboxylic acid 2-tert-butyl ester 4-ethyl ester

Product 1

HCID 498404632-O-tert-butyl 4-O-ethyl 5-(4-bromobutyl)-3-methyl-1H-pyrrole-2,4-dicarboxylateYield 70%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

5-(4-Bromo-but-1-enyl)-3-methyl-1H-pyrrole-2,4-dicarboxylic acid 2-tert-butyl ester 4-ethyl ester 60b (30 mg, 0.08 mmol) was dissolved in 3 ml of ethanol under stirring, and added with palladium on activated carbon (6 mg, 5%) to the solution at room temperature. The reaction mixture was stirred for 45 minutes under a hydrogen atmosphere. After thin lay chromatography showed the disappearance of starting materials, the reaction mixture was filtered, concentrated under reduced pressure to obtain the title compound 5-(4-bromo-butyl)-3-methyl-1H-pyrrole-2,4-dicarboxylic acid 2-tert-butyl ester 4-ethyl ester 60c (21 mg, yield 70%) as a colorless oil.

Workup

  1. stirringThe reaction mixture was stirred for 45 minutes under a hydrogen atmosphere
  2. filtrationthe reaction mixture was filtered
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7824b28c8c194283920793fef6b8b628
Source dataset
uspto-grants-2012_12
Patent number
US08329682B2

Reaction notes

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