Dimethylformamide → 4-(4-Amino-3-fluorophenoxy)-7-oxiranylmethoxyquinoline-6-carbonitrile

HRID 1010338Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1010338
CN(C)C=O.[CH2:6]([CH:8]1[O:10][CH2:9]1)Br.C(=O)([O-])[O-].[K+].[K+].[NH2:17][C:18]1[CH:37]=[CH:36][C:21]([O:22][C:23]2[C:32]3[C:27](=[CH:28][C:29]([OH:35])=[C:30]([C:33]#[N:34])[CH:31]=3)[N:26]=[CH:25][CH:24]=2)=[CH:20][C:19]=1[F:38]>C(OCC)(=O)C.O>[NH2:17][C:18]1[CH:37]=[CH:36][C:21]([O:22][C:23]2[C:32]3[C:27](=[CH:28][C:29]([O:35][CH2:6][CH:8]4[CH2:9][O:10]4)=[C:30]([C:33]#[N:34])[CH:31]=3)[N:26]=[CH:25][CH:24]=2)=[CH:20][C:19]=1[F:38]

Komponenten

7

Edukt 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 18430EpibromohydrinHCID 1358293794-(4-Amino-3-fluorophenoxy)-6-cyano-7-hydroxyquinoline

Produkt 1

HCID 229362494-(4-Amino-3-fluorophenoxy)-7-oxiranylmethoxyquinoline-6-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

After adding dimethylformamide (6 ml), epibromohydrin (1.3 ml) and potassium carbonate (380 mg) to 4-(4-amino-3-fluorophenoxy)-6-cyano-7-hydroxyquinoline (400 mg), the mixture was stirred overnight at room temperature. Water was added to the reaction solution, extraction was performed with ethyl acetate, and then the organic layer was washed with water and saturated brine in that order and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain the title compound (400 mg).

Aufarbeitung

  1. washthe organic layer was washed with water and saturated brine in that order
  2. dry with materialdried over anhydrous sodium sulfate
  3. distillationthe solvent was distilled off under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-824251f496c644169ae6475ad476ef92
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07973160B2

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