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

HRID 77435노트

반응식

HRID 77435 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-7cde85bd8a7b4a1b8b8ff65fca89fac4
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841305B2

반응 노트

불러오는 중…