Sodium Iodide → 4-bromo-1-ethyl-5-(4-phthalimidobutyl)-1H-pyrazole-3-carbonitrile

HRID 1984358

반응식

HRID 1984358 반응식
[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[K].[I-].[Na+].[Br:15][C:16]1[C:17]([C:28]#[N:29])=[N:18][N:19]([CH2:26][CH3:27])[C:20]=1[CH2:21][CH2:22][CH2:23][CH2:24]Cl>C(Cl)(Cl)Cl.O.CN(C=O)C>[Br:15][C:16]1[C:17]([C:28]#[N:29])=[N:18][N:19]([CH2:26][CH3:27])[C:20]=1[CH2:21][CH2:22][CH2:23][CH2:24][N:5]1[C:1](=[O:11])[C:2]2=[CH:10][CH:9]=[CH:8][CH:7]=[C:3]2[C:4]1=[O:6]

참가 물질

7

반응물 3

HCID 5238Sodium Iodide2회HCID 24194345Phthalimide potassium salt2회HCID 669582654-bromo-5-(4-chlorobutyl)-1-ethyl-1H-pyrazole-3-carbonitrile

생성물 1

HCID 669584184-bromo-1-ethyl-5-(4-phthalimidobutyl)-1H-pyrazole-3-carbonitrile수율 71.1%

시약·촉매·용매 3

HCID 962Water용매2회HCID 6212Chloroform용매HCID 6228Dimethylformamide용매2회

반응 조건

온도
100 °C

실험 절차

Potassium phthalimide (954 mg, 5.15 mmol), sodium iodide (130 mg, 0.86 mmol), and DMF (5 mL) were added to 4-bromo-5-(4-chlorobutyl)-1-ethyl-1H-pyrazole-3-carbonitrile (1.0 g, 3.4 mmol, prepared as described in Parts A-E of Example 19), and the reaction was heated at 100° C. for 45 minutes under a nitrogen atmosphere and allowed to cool to ambient temperature. Water (50 mL) was added, and the resulting mixture was stirred at 0° C. A precipitate formed, was isolated by filtration, and was dissolved in chloroform. The resulting solution was dried over sodium sulfate, filtered, and concentrated under reduced pressure. An analysis by nuclear resonance spectroscopy (NMR) indicated that starting material was present. The solid was treated with potassium phthalimide (1.27 g, 6.88 mmol), sodium iodide (130 mg, 0.86 mmol), and DMF (5 mL) and heated at 90° C. for three hours. Water (50 mL) was added, and the resulting solid was isolated by filtration to provide 0.97 g of 4-bromo-1-ethyl-5-(4-phthalimidobutyl)-1H-pyrazole-3-carbonitrile as a gray, crystalline solid.

후처리

  1. temperatureto cool to ambient temperature
  2. customA precipitate formed
  3. customwas isolated by filtration
  4. dry with materialThe resulting solution was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. temperatureheated at 90° C. for three hours
  8. customthe resulting solid was isolated by filtration

출처 및 근거

ORD 기록
ord-cefe8cda0a8443deb6cdaf70932fc632
출처 데이터셋
uspto-grants-2009_06
특허 번호
US07544697B2

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