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

HRID 1962483Notes

Reaction equation

HRID 1962483 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-d2a981a3792a41eebc9f46a2cf895b27
Source dataset
uspto-grants-2013_04
Patent number
US08415368B2

Reaction notes

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