Ethyl 2-chloro-5-(2-fluorophenyl)-1H-pyrrole-3-carboxylate → Ethyl 5-(2-fluorophenyl)-1H-pyrrole-3-carboxylate

HRID 2196882Notes

Reaction equation

HRID 2196882 reaction equation
Cl[C:2]1[NH:3][C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[F:18])=[CH:5][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8]>C(O)C.[C].[Pd]>[F:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[C:4]1[NH:3][CH:2]=[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH:5]=1

Participants

4

Reactant 1

HCID 66924835Ethyl 2-chloro-5-(2-fluorophenyl)-1H-pyrrole-3-carboxylate

Product 1

HCID 66924698Ethyl 5-(2-fluorophenyl)-1H-pyrrole-3-carboxylateYield 18.3%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

To a solution (80 mL) of ethyl 2-chloro-5-(2-fluorophenyl)-1H-pyrrole-3-carboxylate (8.6 g) in ethanol was added 10% palladium carbon (50% containing water, 0.86 g), and the mixture was stirred under a hydrogen atmosphere at room temperature for 36 hr. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. The residue was dissolved in ethanol (70 mL), 10% palladium carbon (50% containing water, 0.90 g) was added, and the mixture was stirred under a hydrogen atmosphere at room temperature for 60 hr. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=10:1→5:1) to give the title compound as a brown solid (yield 1.37 g, 18%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in ethanol (70 mL)
  4. addition10% palladium carbon (50% containing water, 0.90 g) was added
  5. stirringthe mixture was stirred under a hydrogen atmosphere at room temperature for 60 hr
  6. filtrationThe reaction mixture was filtered
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=10:1→5:1)

Sources & evidence

ORD record
ord-78fb3cac2b0941088ff7ddc1bee9e95a
Source dataset
uspto-grants-2012_12
Patent number
US08338461B2

Reaction notes

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