Acetate → 4-((E)-2-(1-(1-Ethoxyethyl)-1H-pyrazol-4-yl) vinyl)benzonitrile

HRID 561247

反応式

HRID 561247 の反応式
[CH2:1]([O:3][CH:4]([N:6]1[CH:10]=[C:9](I)[CH:8]=[N:7]1)[CH3:5])[CH3:2].[CH:12]([C:14]1[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][CH:15]=1)=[CH2:13].[Br-].C([O-])(=O)C.C(=O)([O-])[O-].[K+].[K+]>>[CH2:1]([O:3][CH:4]([N:6]1[CH:10]=[C:9](/[CH:13]=[CH:12]/[C:14]2[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][CH:15]=2)[CH:8]=[N:7]1)[CH3:5])[CH3:2]

参加物

6

反応物 5

HCID 175AcetateHCID 259Bromide ionHCID 11430Potassium CarbonateHCID 769674-EthenylbenzonitrileHCID 46404091-(1-Ethoxyethyl)-4-iodo-1H-pyrazole

生成物 1

HCID 669995924-((E)-2-(1-(1-Ethoxyethyl)-1H-pyrazol-4-yl) vinyl)benzonitrile収率 67.6%

実験手順

1-(1-Ethoxyethyl)-4-iodo-1H-pyrazole obtained in Step 1 (162.0 mg) was suspended in N,N-methylformamide (5.0 mL), and added thereto were 4-vinylbenzonitrile (157.3 mg), tetrabutylamonuim bromide (19.6 mg), paladium acetate (41.0 mg) and potassium carbonate (210.4 mg). The mixture was stirred at room temperature for 10 minutes, and subjected to microwave irradiation at 140° C. for 20 minutes. After completion of the reaction, the resulting mixture was filtered through silica gel, and extracted with ethyl acetate (15 mL). The extract was washed successively with saturated ammonium chloride (15 mL) and brine (15 mL). The organic layer was dried over anhydrous magnesium sulfate and concentrated by evaporation under a reduced pressure. The resulting residue was purified by silica gel chromatography to obtain the title compound (0.11 g, yield 61%).

後処理

  1. additionadded
  2. customirradiation at 140° C. for 20 minutes
  3. customAfter completion of the reaction
  4. filtrationthe resulting mixture was filtered through silica gel
  5. extractionextracted with ethyl acetate (15 mL)
  6. washThe extract was washed successively with saturated ammonium chloride (15 mL) and brine (15 mL)
  7. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  8. concentrationconcentrated by evaporation under a reduced pressure
  9. customThe resulting residue was purified by silica gel chromatography

出典と根拠

ORDレコード
ord-580cdbf9bae14f57b9f252631e345925
出典データセット
uspto-grants-2011_11
特許番号
US08063229B2

関連ノート

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