Lithium diisopropylamide → HCID 59700616, Verbindung

HRID 902008

Reaktionsgleichung

Reaktionsgleichung von HRID 902008
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[CH:9][CH:8]=[C:7]2[CH3:14])[CH3:2].C([N-]C(C)C)(C)C.[Li+].CON(C)[C:26]([C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([CH3:34])[N:29]=1)=[O:27]>C1COCC1>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[CH:9][CH:8]=[C:7]2[CH2:14][C:26]([C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([CH3:34])[N:29]=1)=[O:27])[CH3:2]

Komponenten

5

Edukt 3

HCID 2724682Lithium diisopropylamideHCID 109652526-ethoxy-4-methyl-quinolineHCID 45869585N-methoxy-N,6-dimethylpyridine-2-carboxamide

Produkt 1

HCID 59700616HCID 59700616, VerbindungAusbeute 20 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 6-ethoxy-4-methyl-quinoline (360 mg, 2.0 mmol) in THF at −78° C. add 1.5M lithium diisopropylamide (4.6 ml, 7.0 mmol) dropwise and stir for 1 hour. 6-Methyl-pyridine-2-carboxylic acid methoxy-methyl-amide (430 mg, 2.4 mmol) is then added, and the mixture stirred for 30 minutes at −78° C. before quenching with 1N HCl (5 ml). Neutralize with saturated aqueous NaHCO3 and extract with EtOAc (3×50 ml). The organic phase is then dried with MgSO4 and concentrated in vacuo. The crude product was chromatographed on silica gel (elute with 50/50 Hexane/EtOAc) to give 120 mg (20%) of the title compound. MS ES+ m/e 307.1 (M+1).

Aufarbeitung

  1. stirringthe mixture stirred for 30 minutes at −78° C.
  2. custombefore quenching with 1N HCl (5 ml)
  3. extractionNeutralize with saturated aqueous NaHCO3 and extract with EtOAc (3×50 ml)
  4. dry with materialThe organic phase is then dried with MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe crude product was chromatographed on silica gel (elute with 50/50 Hexane/EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-1e59d094cba2480e8ab00ff219a5a1f6
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07365066B2

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