8-Fluoro-2-isopropenyl-4-methyl-3-(4-pyrazol-1-ylbenzyl)quinolin-5-ol → 8-Fluoro-2-isopropyl-4-methyl-3-(4-pyrazol-1-ylbenzyl)quinolin-5-ol

HRID 1944364Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1944364
[F:1][C:2]1[C:11]2[N:10]=[C:9]([C:12]([CH3:14])=[CH2:13])[C:8]([CH2:15][C:16]3[CH:21]=[CH:20][C:19]([N:22]4[CH:26]=[CH:25][CH:24]=[N:23]4)=[CH:18][CH:17]=3)=[C:7]([CH3:27])[C:6]=2[C:5]([OH:28])=[CH:4][CH:3]=1>[OH-].[Pd+2].[OH-].CO>[F:1][C:2]1[C:11]2[N:10]=[C:9]([CH:12]([CH3:13])[CH3:14])[C:8]([CH2:15][C:16]3[CH:21]=[CH:20][C:19]([N:22]4[CH:26]=[CH:25][CH:24]=[N:23]4)=[CH:18][CH:17]=3)=[C:7]([CH3:27])[C:6]=2[C:5]([OH:28])=[CH:4][CH:3]=1

Komponenten

4

Edukt 1

HCID 1363483598-Fluoro-2-isopropenyl-4-methyl-3-(4-pyrazol-1-ylbenzyl)quinolin-5-ol

Produkt 1

HCID 1363309328-Fluoro-2-isopropyl-4-methyl-3-(4-pyrazol-1-ylbenzyl)quinolin-5-olAusbeute 58,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9942167Palladium hydroxideKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of 8-fluoro-2-isopropenyl-4-methyl-3-(4-pyrazol-1-ylbenzyl)quinolin-5-ol (0.13 g), palladium hydroxide (0.047 g) and methanol (3.4 mL) was stirred at room temperature for 20 hours under an atmosphere of hydrogen. The mixture was filtered through Celite and concentrated under reduced pressure. Purification of the residue by column chromatography on silica gel, eluting with a mixture of cyclohexane and ethyl acetate (1:0 to 1:1 by volume) gave title compound as a white foam (0.077 g).

Aufarbeitung

  1. filtrationThe mixture was filtered through Celite
  2. concentrationconcentrated under reduced pressure
  3. customPurification of the residue by column chromatography on silica gel
  4. washeluting with a mixture of cyclohexane and ethyl acetate (1:0 to 1:1 by volume)

Quellen und Nachweise

ORD-Eintrag
ord-b07c9124834f4650b0474ff3ec0d1717
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08394830B2

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