Potassium Carbonate → Methyl 4-methyl-1-phenyl-1H-pyrrole-3-carboxylate

HRID 1670858Notes

Reaction equation

HRID 1670858 reaction equation
[CH3:1][C:2]1[C:3]([C:7]([O:9][CH3:10])=[O:8])=[CH:4][NH:5][CH:6]=1.I[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+].N1CCC[C@H]1C(O)=O>CN(C)C=O.[Cu](I)I>[CH3:1][C:2]1[C:3]([C:7]([O:9][CH3:10])=[O:8])=[CH:4][N:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 11575IodobenzeneHCID 145742L-ProlineHCID 15274278Methyl 4-methyl-1H-pyrrole-3-carboxylate

Product 1

HCID 57687732Methyl 4-methyl-1-phenyl-1H-pyrrole-3-carboxylateYield 35%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl 4-methyl-1H-pyrrole-3-carboxylate (1.70 g) in N,N-dimethylformamide (1.5 mL) were added iodobenzene (1.50 mL), potassium carbonate (2.19 g), L-proline (273 mmg) and copper iodide (232 mg), and the reaction was carried out in a microwave reactor (Emrys Optimizer manufactured by Personal Chemistry, 70° C., 1 hr). The reaction mixture was filtered through celite, water was added to the filtrate, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=9:1→2:1) to give the title compound as a colorless solid (yield 925 mg, 35%).

Workup

  1. customthe reaction was carried out in a microwave reactor
  2. custom(Emrys Optimizer manufactured by Personal Chemistry, 70° C., 1 hr)
  3. filtrationThe reaction mixture was filtered through celite, water
  4. additionwas added to the filtrate
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe extract was washed with saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=9:1→2:1)

Sources & evidence

ORD record
ord-9f9ae0f3f0bb41f99228a2a7b339b46a
Source dataset
uspto-grants-2011_08
Patent number
US07994205B2

Reaction notes

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