Triethylamine → methyl 4-fluoro-5-phenyl-1H-pyrrole-3-carboxylate

HRID 2090681Notes

Reaction equation

HRID 2090681 reaction equation
Cl[C:2]1[NH:3][C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:5]([F:11])[C:6]=1[C:7]([O:9][CH3:10])=[O:8].C(N(CC)CC)C>CO.[C].[Pd]>[F:11][C:5]1[C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:2][NH:3][C:4]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 66974454methyl 2-chloro-4-fluoro-5-phenyl-1H-pyrrole-3-carboxylate

Product 1

HCID 66974524methyl 4-fluoro-5-phenyl-1H-pyrrole-3-carboxylateYield 86,784.898%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

Methyl 2-chloro-4-fluoro-5-phenyl-1H-pyrrole-3-carboxylate (0.92 mg), 10% palladium carbon (50% containing water, 0.20 g) and triethylamine (0.56 mL) were suspended in methanol (30 mL), and the mixture was stirred under a hydrogen atmosphere at room temperature for 2 hr. The reaction mixture was filtered through celite, and the insoluble material was washed with ethyl acetate. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=19:1→1:1) to give the title compound as a colorless solid (yield 0.69 g, 87%).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. washthe insoluble material was washed with ethyl acetate
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=19:1→1:1)

Sources & evidence

ORD record
ord-5802b438d2354eea89a469865f522709
Source dataset
uspto-grants-2013_05
Patent number
US08436187B2

Reaction notes

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