Dimethylformamide → HCID 15110858, compound

HRID 339722Notes

Reaction equation

HRID 339722 reaction equation
[Br:1][C:2]1[C:3]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:4]([CH3:13])[NH:5][C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH3:19]N(C=O)C.[H-].[Na+].CI>[Cl-].[Na+].O>[Br:1][C:2]1[C:3]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:4]([CH3:13])[N:5]([CH3:19])[C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 12303549HCID 12303549, compound

Product 1

HCID 15110858HCID 15110858, compoundYield 115%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
0 °C

Procedure

Ethyl 4-bromo-2-methyl-5-phenyl-1H-pyrrole-3-carboxylate (3.31 g, 11.4 mmol) was dissolved into anhydrous DMF (50 mL). After stirring at 0° C. for 15 min, to this solution was added NaH (60%, 0.55 g, 13.7 mmol). The mixture was held at 0° C. for 10 min and then MeI (2.13 mL, 34.2 mmol) was added to the mixture. The reaction mixture was gradually warmed to RT and stirred overnight. The mixture was poured into brine (100 mL) and extracted with ethyl acetate (200 mL). The organic phase was dried over MgSO4 and evaporated under vacuum. The residue was further purified by flash column chromatography to provide the crude intermediate ethyl 4-bromo-1,2-dimethyl-5-phenyl-1H-pyrrole-3-carboxylate (4.23 g, 13.1 mmol, 115%).

Workup

  1. waitThe mixture was held at 0° C. for 10 min
  2. temperatureThe reaction mixture was gradually warmed to RT
  3. stirringstirred overnight
  4. extractionextracted with ethyl acetate (200 mL)
  5. dry with materialThe organic phase was dried over MgSO4
  6. customevaporated under vacuum
  7. customThe residue was further purified by flash column chromatography

Sources & evidence

ORD record
ord-cea2b07c6499435280243d72c6921988
Source dataset
uspto-grants-2014_11
Patent number
US08895558B2

Reaction notes

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