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

HRID 1962557

Reaction equation

HRID 1962557 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-4f584b1789164a2fb824fb63b84e56cd
Source dataset
uspto-grants-2013_04
Patent number
US08415368B2

Linked notes

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