HCID 66924730, compound → HCID 66924945, compound

HRID 554220Notes

Reaction equation

HRID 554220 reaction equation
Cl[C:2]1[NH:3][C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:5]([F:12])[C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8]>C(O)C.[C].[Pd]>[F:12][C:5]1[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:2][NH:3][C:4]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 1

HCID 66924730HCID 66924730, compound

Product 1

HCID 66924945HCID 66924945, compoundYield 38.3%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

To a solution (30 mL) of ethyl 2-chloro-4-fluoro-5-phenyl-1H-pyrrole-3-carboxylate (300 mg) in ethanol was added 10% palladium carbon (50% water-containing product, 0.3 g), and the mixture was stirred under a hydrogen atmosphere at room temperature for 24 hr. The reaction mixture was filtrated, 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 a colorless oil (yield 100 mg, 38%).

Workup

  1. filtrationThe reaction mixture was filtrated
  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-b71c0233008a482ca39406a8ade8c307
Source dataset
uspto-grants-2011_11
Patent number
US08048909B2

Reaction notes

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