HCID 67254019, compound → Methyl 4-methyl-5-(2-(trifluoromethyl)phenyl)-1H-pyrrole-3-carboxylate

HRID 383748Notes

Reaction equation

HRID 383748 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[C:9]([CH3:10])=[C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[C:17]([F:20])([F:19])[F:18])[NH:7][CH2:6]1)=[O:4]>C1(C)C=CC=CC=1.[Pd]>[CH3:1][O:2][C:3]([C:5]1[C:9]([CH3:10])=[C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[C:17]([F:20])([F:19])[F:18])[NH:7][CH:6]=1)=[O:4]

Participants

4

Reactant 1

HCID 67254019HCID 67254019, compound

Product 1

HCID 67251895Methyl 4-methyl-5-(2-(trifluoromethyl)phenyl)-1H-pyrrole-3-carboxylateYield 29.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1140TolueneSolvent

Procedure

To a solution of 4-methyl-5-(2-trifluoromethyl-phenyl)-2,3-dihydro-1H-pyrrole-3-carboxylic acid methyl ester (10 g, 35 mmol) in toluene was added 10% Pd/C (3.3 g). The resulting suspension was heated to reflux for 3 days. After cooling, the solids were removed by filtration. The filtrate was washed with toluene and concentrated under reduced pressure to yield an oil, which was purified by column chromatography (silica), eluting with EtOAc-hexane (1:1) to give the title compound (2.9 g, 29%). MS (ES): 284 (MH+).

Workup

  1. temperatureThe resulting suspension was heated
  2. temperatureto reflux for 3 days
  3. temperatureAfter cooling
  4. customthe solids were removed by filtration
  5. washThe filtrate was washed with toluene
  6. concentrationconcentrated under reduced pressure
  7. customto yield an oil, which
  8. customwas purified by column chromatography (silica)
  9. washeluting with EtOAc-hexane (1:1)

Sources & evidence

ORD record
ord-afe6d48b9f584016bc0536ccbd3c0ebe
Source dataset
uspto-grants-2013_02
Patent number
US08367667B2

Reaction notes

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