Methyl iodide → methyl 1H-pyrrole-3-carboxylate

HRID 1435441Notes

Reaction equation

HRID 1435441 reaction equation
[C:1](=O)([O-])[O-].[K+].[K+].[NH:7]1[CH:11]=[CH:10][C:9]([C:12]([OH:14])=[O:13])=[CH:8]1.CI>CN(C=O)C.O>[NH:7]1[CH:11]=[CH:10][C:9]([C:12]([O:14][CH3:1])=[O:13])=[CH:8]1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 101030Pyrrole-3-carboxylic acid

Product 1

HCID 12361759methyl 1H-pyrrole-3-carboxylateYield 30.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (0.65 g, 5.4 mmol) was added to a solution of 1H-pyrrole-3-carboxylic acid (0.50 g, 4.5 mmol) in DMF (10 mL). Stirring for 2 h at room temperature, methyl iodide (0.34 mL, 0.77 g, 5.4 mmol) was added. The mixture was stirred overnight at room temperature, diluted with H2O (50 mL), and extracted with EtOAc (3×50 mL). The combined organic phases were washed with NaCl (10 mL) and dried over Na2SO4. The crude product was purified by MPLC using Hex/EtOAc (7:3) on silica gel to give 0.17 g (30%) of a white solid as the title compound. 1H NMR (400 MHz, CHLOROFORM-D) δ 3.82 (s, 3 H), 6.56-6.72 (m, 1 H), 6.73-6.83 (m, 1 H), 7.36-7.50 (m, 1 H).

Workup

  1. stirringThe mixture was stirred overnight at room temperature
  2. extractionextracted with EtOAc (3×50 mL)
  3. washThe combined organic phases were washed with NaCl (10 mL)
  4. dry with materialdried over Na2SO4
  5. customThe crude product was purified by MPLC

Sources & evidence

ORD record
ord-773a03e86d5b4e3c83cc03ba24f2efae
Source dataset
uspto-grants-2009_11
Patent number
US07615642B2

Reaction notes

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