Methyl iodide → HCID 66914796, compound

HRID 880435Notes

Reaction equation

HRID 880435 reaction equation
[H-].[Na+].[Br:3][C:4]1[C:5]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:6]([C:10]([O-:12])=[O:11])[NH:7][C:8]=1[CH3:9].[CH3:19]I.O1CC[CH2:23][CH2:22]1>>[Br:3][C:4]1[C:5]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:6]([C:10]([O:12][CH2:22][CH3:23])=[O:11])[N:7]([CH3:19])[C:8]=1[CH3:9]

Participants

5

Reactant 4

HCID 6328Methyl iodideHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 86654665HCID 86654665, compound

Product 1

HCID 66914796HCID 66914796, compoundYield 98%

Conditions

Temperature
0 °C

Procedure

60% Sodium hydride (320 mg, 8.03 mmol) in mineral oil was added to a solution of 4-bromo-5-methyl-3-phenyl-1H-pyrrole-2-carboxylate (1.65 g, 5.36 mmol) in tetrahydrofuran (20 mL) at 0° C. The reaction mixture was stirred at 0° C. for 15 min and then the methyl iodide (0.66 mL, 10.72 mmol) was added at 0° C. and then the reaction mixture was allowed to warm to room temperature overnight. The reaction mixture was quenched with ice and the solvent was evaporated. The organics were extracted with ethyl acetate and the organic layer was washed with water, brine and dried over anhydrous sodium sulfate. The ethyl acetate layer was concentrated under reduced pressure to afford ethyl 4-bromo-1,5-dimethyl-3-phenyl-pyrrole-2-carboxylate (1.68 g, 98%) as a liquid.

Workup

  1. temperatureto warm to room temperature overnight
  2. customThe reaction mixture was quenched with ice
  3. customthe solvent was evaporated
  4. extractionThe organics were extracted with ethyl acetate
  5. washthe organic layer was washed with water, brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationThe ethyl acetate layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-053b0b96d8d843ffb7827dff3d11688b
Source dataset
uspto-grants-2015_03
Patent number
US08993574B2

Reaction notes

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