Hydrochloric Acid → HCID 18674996, Verbindung

HRID 1634887Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1634887
Br[CH2:2][Mg].Cl[C:5]1[CH:10]=[C:9]([C:11]2[CH:16]=[C:15]([O:17][CH3:18])[C:14]([O:19][CH3:20])=[C:13]([O:21][CH3:22])[CH:12]=2)[CH:8]=[CH:7][N:6]=1.Cl>[Ni](Cl)Cl.C1COCC1>[CH3:2][C:5]1[CH:10]=[C:9]([C:11]2[CH:16]=[C:15]([O:17][CH3:18])[C:14]([O:19][CH3:20])=[C:13]([O:21][CH3:22])[CH:12]=2)[CH:8]=[CH:7][N:6]=1

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 186749672-Chloro-4-(3,4,5-trimethoxyphenyl)pyridineHCID 178507037HCID 178507037, Verbindung

Produkt 1

HCID 18674996HCID 18674996, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24385Nickel DichlorideKatalysatorHCID 8028TetrahydrofuranLösungsmittel3×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Nickel chloride (3.0 mg) was added to THF (1 mL) under an argon atmosphere, and the mixture was kept at 0° C. To the mixture, a THF solution (0.38 mL) of 0.93 M bromomethylmagnesium was slowly added, and a THF solution (2 mL) of 2-chloro-4-(3,4,5-Trimethoxyphenyl)pyridine (50 mg) was then slowly added. The mixture was stirred at 0° C. for 10 minutes and then at 70° C. for 1.5 hours. A small amount was diluted hydrochloric acid was added to the reaction mixture at 0° C. to conduct extraction with ethyl acetate. The resultant organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate and saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (dichloromethane:methanol=15:1) to obtain the title compound.

Aufarbeitung

  1. customwas kept at 0° C
  2. waitat 70° C. for 1.5 hours
  3. additionwas added to the reaction mixture at 0° C.
  4. extractionextraction with ethyl acetate
  5. washThe resultant organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate and saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by column chromatography on silica gel (dichloromethane:methanol=15:1)

Quellen und Nachweise

ORD-Eintrag
ord-2affa49d60454924a8d663b5d47f5ca5
Quelldatensatz
uspto-grants-2003_01
Patentnummer
US06509329B1

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