Boron tribromide → 4-[4-(4-Ethyl-5-fluoro-2-hydroxyphenoxy)-3-fluorobenzoyl]-1-methylpiperazin-2-one

HRID 389992Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 389992
B(Br)(Br)Br.[CH2:5]([C:7]1[C:30]([F:31])=[CH:29][C:10]([O:11][C:12]2[CH:27]=[CH:26][C:15]([C:16]([N:18]3[CH2:23][CH2:22][N:21]([CH3:24])[C:20](=[O:25])[CH2:19]3)=[O:17])=[CH:14][C:13]=2[F:28])=[C:9]([O:32]C)[CH:8]=1)[CH3:6].[Cl-].[NH4+]>ClCCl>[CH2:5]([C:7]1[C:30]([F:31])=[CH:29][C:10]([O:11][C:12]2[CH:27]=[CH:26][C:15]([C:16]([N:18]3[CH2:23][CH2:22][N:21]([CH3:24])[C:20](=[O:25])[CH2:19]3)=[O:17])=[CH:14][C:13]=2[F:28])=[C:9]([OH:32])[CH:8]=1)[CH3:6]

Komponenten

5

Edukt 3

HCID 25134Boron tribromideHCID 25517Ammonium ChlorideHCID 671162384-[4-(4-Ethyl-5-fluoro-2-methoxyphenoxy)-3-fluorobenzoyl]-1-methylpiperazin-2-one

Produkt 1

HCID 513565014-[4-(4-Ethyl-5-fluoro-2-hydroxyphenoxy)-3-fluorobenzoyl]-1-methylpiperazin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A commercial solution of boron tribromide (1N in DCM, 1.33 mL, 1.32 mmol) was added to a solution of 4-[4-(4-ethyl-5-fluoro-2-methoxyphenoxy)-3-fluorobenzoyl]-1-methylpiperazin-2-one (which may be prepared in accordance with the experimental described in Example 5, step 2; 200 mg, 0.49 mmol) in dichloromethane (1.6 mL) placed under argon at −30° C. The reaction mixture was stirred at room temperature overnight and diluted by addition of dichloromethane (30 mL) and a saturated solution of ammonium chloride (30 mL). After separation, the aqueous layer was extracted with dichloromethane (2×30 mL). The combined organic phases were dried over sodium sulfate, filtered and concentrated under vacuum. The residue was purified by chromatography on silica gel, using dichloromethane/methanol (95:5) as eluent. The title product was obtained as a yellow solid (135 mg, 70%).

Aufarbeitung

  1. custommay be prepared in accordance with the
  2. customplaced under argon at −30° C
  3. customAfter separation
  4. extractionthe aqueous layer was extracted with dichloromethane (2×30 mL)
  5. dry with materialThe combined organic phases were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customThe residue was purified by chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-53f78cebaf21498b857456c1ddb41dae
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08383621B2

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