4-(Bromoacetyl)benzonitrile → 4-{[5-Oxo-4,4-bis-pyridin-4-ylmethyl-1-(2,6,6-trimethyl-bicyclo[3.1.1]hept-3-ylmethyl)-imidazolidin-2-ylidene]-acetyl}-benzonitrile

HRID 1420787

Reaktionsgleichung

Reaktionsgleichung von HRID 1420787
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][C:8]2([CH2:26][C:27]3[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=3)[NH:12][C:11](=S)[N:10]([CH2:14][CH:15]3[CH2:20][CH:19]4[CH2:21][CH:17]([C:18]4([CH3:23])[CH3:22])[CH:16]3[CH3:24])[C:9]2=[O:25])=[CH:3][CH:2]=1.C[Si]([N-][Si](C)(C)C)(C)C.[K+].[C:43]([C:45]1[CH:54]=[CH:53][C:48]([C:49](=[O:52])[CH2:50]Br)=[CH:47][CH:46]=1)#[N:44]>C1COCC1>[O:25]=[C:9]1[N:10]([CH2:14][CH:15]2[CH2:20][CH:19]3[CH2:21][CH:17]([C:18]3([CH3:23])[CH3:22])[CH:16]2[CH3:24])[C:11](=[CH:50][C:49]([C:48]2[CH:53]=[CH:54][C:45]([C:43]#[N:44])=[CH:46][CH:47]=2)=[O:52])[NH:12][C:8]1([CH2:26][C:27]1[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=1)[CH2:7][C:4]1[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=1

Komponenten

5

Edukt 3

HCID 986544-(Bromoacetyl)benzonitrileHCID 3251421Potassium bis(trimethylsilyl)amideHCID 154627795,5-Bis-pyridin-4-ylmethyl-2-thioxo-3-(2,6,6-trimethyl-bicyclo[3.1.1]hept-3-ylmethyl)-imidazolidin-4-one

Produkt 1

HCID 700192994-{[5-Oxo-4,4-bis-pyridin-4-ylmethyl-1-(2,6,6-trimethyl-bicyclo[3.1.1]hept-3-ylmethyl)-imidazolidin-2-ylidene]-acetyl}-benzonitrileAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

5,5-Bis-pyridin-4-ylmethyl-2-thioxo-3-(2,6,6-trimethyl-bicyclo[3.1.1]hept-3-ylmethyl)-imidazolidin-4-one (101 mg, 0.225 mmol) was dissolved in anhydrous THF (3.0 ml) under an atmosphere of dry N2. The reaction was then cooled to 0° C. and potassium bis(trimethylsilyl)amide (46.8 mg, 0.235 mmol) was added. After stirring for 15 minutes, 4-cyanophenacyl bromide (51.5 mg, 0.230 mmol) was added to the reaction and the reaction was subsequently stirred for 20 minutes. The mixture was subsequently partitioned between CH2Cl2 and saturated sodium bicarbonate (NaHCO3) solution. The CH2Cl2 layer was dried over Na2SO4, filtered, and concentrated under vacuum to give a yellow oil. The oil was chromatographed on silica gel using 50% ethyl acetate in hexanes to remove unreacted 4-cyanophenacyl bromide and then eluted with 2% methanol in ethyl acetate to give 112 mg (0.189 mmol) of the titled compound as a yellow foam.

Aufarbeitung

  1. stirringthe reaction was subsequently stirred for 20 minutes
  2. customThe mixture was subsequently partitioned between CH2Cl2 and saturated sodium bicarbonate (NaHCO3) solution
  3. dry with materialThe CH2Cl2 layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customto give a yellow oil
  7. customThe oil was chromatographed on silica gel using 50% ethyl acetate in hexanes
  8. customto remove unreacted 4-cyanophenacyl bromide
  9. washeluted with 2% methanol in ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-9d94077ced5b41338101fe8fdf4a8be0
Quelldatensatz
uspto-grants-2000_06
Patentnummer
US06071935

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