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

HRID 1428196Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1428196
[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

Komponenten

7

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-a49cd2d785894474a5e54828b1fe3945
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08937067B2

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