Tetrahydrofuran → 1-(6-bromo-5-(2,4-difluorophenoxy)-1H-indazol-1-yl)-2-methylpropan-2-ol

HRID 912474Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 912474
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][N:8]2[CH2:11][C:12](=[O:14])[CH3:13])=[CH:4][C:3]=1[O:15][C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][C:17]=1[F:23].[CH3:24][Mg]Cl.C1COCC1>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][N:8]2[CH2:11][C:12]([CH3:24])([OH:14])[CH3:13])=[CH:4][C:3]=1[O:15][C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][C:17]=1[F:23]

Komponenten

5

Edukt 3

HCID 8028TetrahydrofuranHCID 674168791-(6-Bromo-5-(2,4-difluorophenoxy)-1H-indazol-1-yl)propan-2-oneHCID 178418332HCID 178418332, Verbindung

Produkt 1

HCID 674164781-(6-bromo-5-(2,4-difluorophenoxy)-1H-indazol-1-yl)-2-methylpropan-2-olAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a stirred solution of 1-(6-Bromo-5-(2,4-difluorophenoxy)-1H-indazol-1-yl)propan-2-one (3.81 g, 10.0 mmol) in toluene (100 mL) at 21° C. was added a 3.0 M solution of methylmagnesium chloride in THF (5.0 mL, 15 mmol) in one portion. The temperature of the resulting solution rose to 34° C. and was stirred without any temperature control. After a total of 60 min the reaction mixture was quenched by addition of saturated ammonium chloride (50 mL). The resulting mixture was vigorously stirred for 20 min, then transferred to a separatory funnel and shaken. The organic layer was dried over sodium sulfate and the solvent removed under reduced pressure to afford the title compound as an orange oil (3.79 g, 96%) that slowly crystallized on standing.

Aufarbeitung

  1. customrose to 34° C.
  2. customAfter a total of 60 min the reaction mixture was quenched by addition of saturated ammonium chloride (50 mL)
  3. stirringThe resulting mixture was vigorously stirred for 20 min
  4. customtransferred to a separatory funnel
  5. stirringshaken
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. customthe solvent removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-592930c06be24d70b616f07817898905
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08026233B2

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