Water → Ethyl 2-bromo-6-formyl-4-methyl-4H-thieno[3,2-b]pyrrole-5-carboxylate

HRID 77435Notes

Reaction equation

HRID 77435 reaction equation
[Br:1][C:2]1[S:9][C:8]2[C:7]([CH:10]=[O:11])=[C:6]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[NH:5][C:4]=2[CH:3]=1.[C:17](=O)([O-])[O-].[K+].[K+].IC.O>CN(C=O)C.CCOC(C)=O>[Br:1][C:2]1[S:9][C:8]2[C:7]([CH:10]=[O:11])=[C:6]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[N:5]([CH3:17])[C:4]=2[CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 58386865Ethyl 2-bromo-6-formyl-4H-thieno[3,2-b]pyrrole-5-carboxylate

Product 1

HCID 58386867Ethyl 2-bromo-6-formyl-4-methyl-4H-thieno[3,2-b]pyrrole-5-carboxylateYield 82%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of aldehyde 62 (515 mg, 1.70 mmol) in DMF (5 mL) was added potassium carbonate (707 mg, 5.12 mmol) and iodomethane (0.27 mL, 3.40 mmol) and the resulting mixture was stirred at room temperature for 2 hr. To the mixture was added H2O (30 mL) and EtOAc (50 mL) and the organic layer was separated and washed with brine and dried over Na2SO4. After removing the organic solvent under reduced pressure, the residue was purified by column chromatography (EtOAc/Hexane: 1/8) to give the desired N-methylated product 63 (440 mg, 82%) as a white solid.

Workup

  1. customthe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. customAfter removing the organic solvent under reduced pressure
  5. customthe residue was purified by column chromatography (EtOAc/Hexane: 1/8)

Sources & evidence

ORD record
ord-7cde85bd8a7b4a1b8b8ff65fca89fac4
Source dataset
uspto-grants-2014_09
Patent number
US08841305B2

Reaction notes

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