Water → methyl 4-iodo-1-methyl-1H-pyrrole-2-carboxylate

HRID 1129

Reaction equation

HRID 1129 reaction equation
[H-].[Na+].[I:3][C:4]1[CH:5]=[C:6]([C:9]([O:11][CH3:12])=[O:10])[NH:7][CH:8]=1.I[CH3:14].O>CN(C=O)C>[CH3:14][N:7]1[CH:8]=[C:4]([I:3])[CH:5]=[C:6]1[C:9]([O:11][CH3:12])=[O:10]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 11673249methyl 4-iodo-1H-pyrrole-2-carboxylate

Product 1

HCID 21826247methyl 4-iodo-1-methyl-1H-pyrrole-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

780 mg (25.9 mmol) of sodium hydride (80% in oil) and 20 ml of DMF were introduced into a three-necked flask, a solution of 6.5 g (25.9 mmol) of methyl 4-iodo-2-pyrrolecarboxylate in 50 ml of DMF was added dropwise and the mixture was stirred until gaseous emission ceased. 2.1 ml (33.6 mmol) of iodomethane were then added and the mixture was stirred at room temperature for two hours. The reaction medium was poured into water, extracted with ethyl ether, the organic phase decanted, dried over magnesium sulfate and evaporated. The residue obtained was purified by chromatography on a silica column eluted with a mixture of dichloromethane and hexane (40/60). 4.5 g (65%) of methyl N-methyl-4-iodo-2-pyrrolecarboxylate of melting point 64°-65° C. were recovered.

Workup

  1. stirringthe mixture was stirred at room temperature for two hours
  2. extractionextracted with ethyl ether
  3. customthe organic phase decanted
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe residue obtained
  7. customwas purified by chromatography on a silica column
  8. washeluted with a mixture of dichloromethane and hexane (40/60)
  9. custom4.5 g (65%) of methyl N-methyl-4-iodo-2-pyrrolecarboxylate of melting point 64°-65° C. were recovered

Sources & evidence

ORD record
ord-8254c501c8dc491b8f88eae119f49eae
Source dataset
uspto-grants-1998_03
Patent number
US05723499

Linked notes

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