Potassium Carbonate → Methyl 4-methyl-1-phenyl-1H-pyrrole-3-carboxylate

HRID 1670858노트

반응식

HRID 1670858 반응식
[CH3:1][C:2]1[C:3]([C:7]([O:9][CH3:10])=[O:8])=[CH:4][NH:5][CH:6]=1.I[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+].N1CCC[C@H]1C(O)=O>CN(C)C=O.[Cu](I)I>[CH3:1][C:2]1[C:3]([C:7]([O:9][CH3:10])=[O:8])=[CH:4][N:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=1

참가 물질

7

반응물 4

HCID 11430Potassium CarbonateHCID 11575IodobenzeneHCID 145742L-ProlineHCID 15274278Methyl 4-methyl-1H-pyrrole-3-carboxylate

생성물 1

HCID 57687732Methyl 4-methyl-1-phenyl-1H-pyrrole-3-carboxylate수율 35%

시약·촉매·용매 2

HCID 83717Copper iodide촉매HCID 6228Dimethylformamide용매

실험 절차

To a solution of methyl 4-methyl-1H-pyrrole-3-carboxylate (1.70 g) in N,N-dimethylformamide (1.5 mL) were added iodobenzene (1.50 mL), potassium carbonate (2.19 g), L-proline (273 mmg) and copper iodide (232 mg), and the reaction was carried out in a microwave reactor (Emrys Optimizer manufactured by Personal Chemistry, 70° C., 1 hr). The reaction mixture was filtered through celite, water was added to the filtrate, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=9:1→2:1) to give the title compound as a colorless solid (yield 925 mg, 35%).

후처리

  1. customthe reaction was carried out in a microwave reactor
  2. custom(Emrys Optimizer manufactured by Personal Chemistry, 70° C., 1 hr)
  3. filtrationThe reaction mixture was filtered through celite, water
  4. additionwas added to the filtrate
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe extract was washed with saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=9:1→2:1)

출처 및 근거

ORD 기록
ord-9f9ae0f3f0bb41f99228a2a7b339b46a
출처 데이터셋
uspto-grants-2011_08
특허 번호
US07994205B2

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