3-Pyridinecarboxaldehyde → 1-(4-Ethylpiperazin-1-yl)-3-[(3-pyridyl)hydroxymethyl]isoquinoline

HRID 1007024Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1007024
[CH2:1]([N:3]1[CH2:8][CH2:7][N:6]([C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=[C:11](Br)[N:10]=2)[CH2:5][CH2:4]1)[CH3:2].[Li]CCCC.[CH:25]([C:27]1[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=1)=[O:26]>O1CCCC1.C(OCC)(=O)C>[CH2:1]([N:3]1[CH2:8][CH2:7][N:6]([C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=[C:11]([CH:25]([C:27]3[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=3)[OH:26])[N:10]=2)[CH2:5][CH2:4]1)[CH3:2]

Komponenten

6

Edukt 3

HCID 103713-PyridinecarboxaldehydeHCID 225024471-(1-Ethylpiperazin-4-yl)-3-bromoisoquinolineHCID 178418339Butyllithium

Produkt 1

HCID 225024871-(4-Ethylpiperazin-1-yl)-3-[(3-pyridyl)hydroxymethyl]isoquinolineAusbeute 35,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 1-(4-ethylpiperazin-1-yl)-3-bromoisoquinoline (0.39 g) obtained in Example 28-2, in tetrahydrofuran (10 ml) was cooled to −78° C., followed by the dropwise addition of 2.5M n-BuLi (0.6 ml). Fifteen minutes later, a solution of 3-formylpyridine (0.2 g) in tetrahydrofuran (3 ml) was added dropwise thereto. The temperature of the reaction solution was gradually raised to room temperature. The reaction solution was diluted with ethyl acetate, washed with brine, water and an aqueous solution of saturated sodium chloride, and dried over magnesium sulfate. The solvent was evaporated, and the resulting residue was purified by silica gel column chromatography (methylene chloride/methanol system), to give the title compound (0.15 g) as a pale yellow oil.

Aufarbeitung

  1. washwashed with brine, water
  2. dry with materialan aqueous solution of saturated sodium chloride, and dried over magnesium sulfate
  3. customThe solvent was evaporated
  4. customthe resulting residue was purified by silica gel column chromatography (methylene chloride/methanol system)

Quellen und Nachweise

ORD-Eintrag
ord-69dddb55453e4541801e9ec757b0528b
Quelldatensatz
uspto-grants-2004_09
Patentnummer
US06790844B2

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