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

HRID 2283757

反応式

HRID 2283757 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-ccbbcce73c014a1791d3fa6e720f7fcb
出典データセット
uspto-grants-2015_09
特許番号
US09145410B2

関連ノート

読み込み中…