Sodium hydride → 1-[5-(4-Chlorophenyl)-6-(2,4-dichlorophenyl)-2-(2,2-dimethylpropanoyl)furo[2,3-b]pyridin-3-yl]pyrrolidin-2-one

HRID 8799

Reaktionsgleichung

Reaktionsgleichung von HRID 8799
[H-].[Na+].Cl[CH2:4][CH2:5][CH2:6][C:7]([NH:9][C:10]1[C:18]2[C:13](=[N:14][C:15]([C:26]3[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][C:27]=3[Cl:33])=[C:16]([C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=3)[CH:17]=2)[O:12][C:11]=1[C:34](=[O:39])[C:35]([CH3:38])([CH3:37])[CH3:36])=[O:8]>C1COCC1>[Cl:25][C:22]1[CH:21]=[CH:20][C:19]([C:16]2[CH:17]=[C:18]3[C:10]([N:9]4[CH2:4][CH2:5][CH2:6][C:7]4=[O:8])=[C:11]([C:34](=[O:39])[C:35]([CH3:37])([CH3:36])[CH3:38])[O:12][C:13]3=[N:14][C:15]=2[C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][C:27]=2[Cl:33])=[CH:24][CH:23]=1

Komponenten

4

Edukt 2

HCID 24758Sodium hydrideHCID 100996934-Chloro-N-[5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)-2-(2,2-dimethylpropanoyl)furo[2,3-b]pyridin-3-yl]butanamide

Produkt 1

HCID 100988381-[5-(4-Chlorophenyl)-6-(2,4-dichlorophenyl)-2-(2,2-dimethylpropanoyl)furo[2,3-b]pyridin-3-yl]pyrrolidin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a magnetically stirred suspension of 7 mg (0.173 mmol) of sodium hydride in 1 mL THF was slowly added 0.100 g (0.173 mmol) of the product of Example 47 dissolved in 1 mL of THF. After 15 min the addition was complete and the reaction mixture was stirred and heated to 60° C. for 3.5 h. The reaction was then cooled to room temperature, and partitioned between saturated aq. NaHCO3 and EtOAc. The organic product was extracted into EtOAc, separated, dried (Na2SO4) filtered and evaporated. The residue was purified on a silica gel flash chromatography column eluted with 0–20% EtOAc-hexane. Evaporation of the purified fractions and drying in vacuo afforded the title compound. HPLC/MS: 541.0 (M+1), 542.9 (M+3); Rt=4.60 min.

Aufarbeitung

  1. additionAfter 15 min the addition
  2. temperatureThe reaction was then cooled to room temperature
  3. custompartitioned between saturated aq. NaHCO3 and EtOAc
  4. extractionThe organic product was extracted into EtOAc
  5. customseparated
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified on a silica gel flash chromatography column
  10. washeluted with 0–20% EtOAc-hexane
  11. customEvaporation of the purified fractions
  12. customdrying in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-06ce1654413a4001b8df472ef7bcb703
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07091216B2

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