Aluminium lithium hydride → 5-Fluoro-2-(3-methyl-benzo[d]isoxazol-6-yloxy)-benzylamine

HRID 1897463Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1897463
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][C:11]2[CH:20]=[CH:19][C:14]3[C:15]([CH3:18])=[N:16][O:17][C:13]=3[CH:12]=2)=[C:6]([CH:9]=1)[C:7]#[N:8].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][C:11]2[CH:20]=[CH:19][C:14]3[C:15]([CH3:18])=[N:16][O:17][C:13]=3[CH:12]=2)=[C:6]([CH:9]=1)[CH2:7][NH2:8]

Komponenten

4

Edukt 2

HCID 21226445Aluminium lithium hydrideHCID 574841185-Fluoro-2-(3-methyl-benzo[d]isoxazol-6-yloxy)-benzonitrile

Produkt 1

HCID 574841195-Fluoro-2-(3-methyl-benzo[d]isoxazol-6-yloxy)-benzylamineAusbeute 78,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

5-fluoro-2-(3-methyl-benzo[d]isoxazol-6-yloxy)-benzonitrile (3v) (84 mg, 0.31 mmol; prepared as described in Example 108) was dissolved in THF (3 mL) and cooled to 0° C. A solution of lithium aluminum hydride in THF (0.35 mL, 0.35 mmol) was added slowly and the reaction was allowed to warm to room temperature. After 1 hour the reaction was quenched by the portion-wise addition of sodium sulfate decahydrate at 0° C. until gas evolution ceased. THF was added and the mixture was filtered through celite and eluted with EtOAc. The solution was concentrated to provide crude product (9v) (66 mg) which was used without further purification.

Aufarbeitung

  1. temperatureto warm to room temperature
  2. customAfter 1 hour the reaction was quenched by the portion-wise addition of sodium sulfate decahydrate at 0° C. until gas evolution
  3. additionTHF was added
  4. filtrationthe mixture was filtered through celite
  5. washeluted with EtOAc
  6. concentrationThe solution was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-68764389ad1d4efcaa1656362845d72b
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08518983B2

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