Methyl iodide → ethyl 5-bromo-1,4-dimethyl-1H-pyrrole-3-carboxylate

HRID 912583Notes

Reaction equation

HRID 912583 reaction equation
[Br:1][C:2]1[NH:6][CH:5]=[C:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[C:3]=1[CH3:12].[H-].[Na+].I[CH3:16]>CN(C=O)C>[Br:1][C:2]1[N:6]([CH3:16])[CH:5]=[C:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[C:3]=1[CH3:12]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 66925114Ethyl 5-bromo-4-methyl-1H-pyrrole-3-carboxylate

Product 1

HCID 59808055ethyl 5-bromo-1,4-dimethyl-1H-pyrrole-3-carboxylateYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of ethyl 5-bromo-4-methyl-1H-pyrrole-3-carboxylate (2.0 g, 8.6 mmol) in anhyd DMF (30 mL) at 0° C. was added portionwise NaH (60% in mineral oil, 705 mg, 17.6 mmol) under nitrogen. After 1 h at ambient temperature, the reaction mixture was charged with iodomethane (1.5 mL, 24 mmol) and then stirred at ambient temperature overnight. The reaction mixture was quenched by cautious addition of water and then extracted with DCM. The combined extracts were washed with water, dried over Na2SO4, concentrated under reduced pressure, and purified by column chromatography, eluting with EtOAc-Hex (0:100 to 20:80), to provide the title compound (1.64 g, 78%) as a white solid. 1H-NMR (CDCl3): δ 7.33 (1H, s), 4.25 (2H, q), 3.58 (3H, s), 2.24 (3H, s), 1.33 (3H, t).

Workup

  1. customThe reaction mixture was quenched by cautious addition of water
  2. extractionextracted with DCM
  3. washThe combined extracts were washed with water
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. custompurified by column chromatography
  7. washeluting with EtOAc-Hex (0:100 to 20:80)

Sources & evidence

ORD record
ord-1d151b5e89754fff887109eb3830173b
Source dataset
uspto-grants-2011_09
Patent number
US08026237B2

Reaction notes

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