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ethyl 2-chloro-5-(2,6-difluorophenyl)-1H-pyrrole-3-carboxylate → ethyl 5-(2,6-difluorophenyl)-1H-pyrrole-3-carboxylate

HRID 2070433
Notes
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Reaction equation

HRID 2070433 reaction equation
Cl[C:2]1[NH:3][C:4]([C:12]2[C:17]([F:18])=[CH:16][CH:15]=[CH:14][C:13]=2[F:19])=[CH:5][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8]>C(O)C.[C].[Pd]>[F:19][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]([F:18])[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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 1

HCID 66974607ethyl 2-chloro-5-(2,6-difluorophenyl)-1H-pyrrole-3-carboxylate

Product 1

HCID 66974572ethyl 5-(2,6-difluorophenyl)-1H-pyrrole-3-carboxylateYield 44%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of ethyl 2-chloro-5-(2,6-difluorophenyl)-1H-pyrrole-3-carboxylate (9.82 g) in ethanol (200 mL) was added 10% palladium carbon (50% containing water, 4.91 g), and the mixture was stirred under a hydrogen atmosphere at 40° C. for 72 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=4:1) to give the title compound as colorless crystals (yield 3.80 g, 24%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=4:1)

Sources & evidence

ORD record
ord-86b9df73108c4696b8810044bc55d403
Source dataset
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08299261B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes