Sodium Iodide → 4-(4-bromo-5-cyano-2-ethyl-2H-pyrazol-3-yl)butyl acetate

HRID 1360432

반응식

HRID 1360432 반응식
[C:1]([O-:4])(=[O:3])[CH3:2].[K+].[I-].[Na+].CN(C=O)C.[Br:13][C:14]1[C:15]([C:26]#[N:27])=[N:16][N:17]([CH2:24][CH3:25])[C:18]=1[CH2:19][CH2:20][CH2:21][CH2:22]Cl>O>[C:1]([O:4][CH2:22][CH2:21][CH2:20][CH2:19][C:18]1[N:17]([CH2:24][CH3:25])[N:16]=[C:15]([C:26]#[N:27])[C:14]=1[Br:13])(=[O:3])[CH3:2]

참가 물질

6

반응물 4

HCID 5238Sodium IodideHCID 6228DimethylformamideHCID 517044Potassium AcetateHCID 669582654-bromo-5-(4-chlorobutyl)-1-ethyl-1H-pyrazole-3-carbonitrile

생성물 1

HCID 669586364-(4-bromo-5-cyano-2-ethyl-2H-pyrazol-3-yl)butyl acetate수율 80.5%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
100 °C

실험 절차

Potassium acetate (1.69 g, 17.2 mmol), sodium iodide (255 mg, 1.7 mmol), and DMF (17 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 two hours under a nitrogen atmosphere and allowed to cool to ambient temperature. Water was added, and the resulting mixture was extracted with diethyl ether. The combined extracts were washed with brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified by chromatography on a HORIZON HPFC system (40+M cartridge, eluting with hexanes/ethyl acetate in a gradient from 90:10 to 60:40) to provide 0.86 g of 4-(4-bromo-5-cyano-2-ethyl-2H-pyrazol-3-yl)butyl acetate.

후처리

  1. temperatureto cool to ambient temperature
  2. extractionthe resulting mixture was extracted with diethyl ether
  3. washThe combined extracts were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by chromatography on a HORIZON HPFC system (40+M cartridge
  8. washeluting with hexanes/ethyl acetate in a gradient from 90:10 to 60:40)

출처 및 근거

ORD 기록
ord-281e0706cfe1425eaca93023ce1cf1c4
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07879849B2

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