Water → 5-[4-(5-Fluoro-2-hydroxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentylamino]-quinoline-2-carboxylic acid diethylamide

HRID 2182722Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2182722
[CH2:1]([N:3]([CH2:37][CH3:38])[C:4]([C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][C:12]=2[NH:16][CH2:17][C:18]([OH:36])([C:32]([F:35])([F:34])[F:33])[CH2:19][C:20]([C:23]2[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:24]=2[O:30]C)([CH3:22])[CH3:21])[N:7]=1)=[O:5])[CH3:2].B(Br)(Br)Br.O>ClCCl>[CH2:37]([N:3]([CH2:1][CH3:2])[C:4]([C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][C:12]=2[NH:16][CH2:17][C:18]([OH:36])([C:32]([F:34])([F:33])[F:35])[CH2:19][C:20]([C:23]2[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:24]=2[OH:30])([CH3:21])[CH3:22])[N:7]=1)=[O:5])[CH3:38]

Komponenten

5

Edukt 3

HCID 962WaterHCID 25134Boron tribromideHCID 207862335-[4-(5-Fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentylamino]quinoline-2-carboxylic acid diethylamide

Produkt 1

HCID 207862325-[4-(5-Fluoro-2-hydroxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentylamino]-quinoline-2-carboxylic acid diethylamideAusbeute 28 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

210 mg (0.39 mmol) of 5-[4-(5-fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentylamino]quinoline-2-carboxylic acid diethylamide is mixed with 7.8 ml (7.8 mmol) of a 1 M boron tribromide solution in dichloromethane. After 20 hours at room temperature, the reaction is halted by adding water. It is extracted with ethyl acetate, the combined organic phases are washed with saturated sodium bicarbonate solution, and it is dried on sodium sulfate. After the solvent is removed and after purification on silica gel with hexane-ethyl acetate (0-100%), 56 mg (28%) of the product is obtained.

Aufarbeitung

  1. extractionIt is extracted with ethyl acetate
  2. washthe combined organic phases are washed with saturated sodium bicarbonate solution, and it
  3. customis dried on sodium sulfate
  4. customAfter the solvent is removed
  5. customafter purification on silica gel with hexane-ethyl acetate (0-100%)

Quellen und Nachweise

ORD-Eintrag
ord-e48bd2d8603142f790a1321b1a3ffd77
Quelldatensatz
uspto-grants-2005_05
Patentnummer
US06897224B2

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