Boron tribromide → 1-(4-{4-[3-(4-Fluoro-phenyl)-5-hydroxymethyl-isoxazol-4-yl]-imidazol-1-yl}-phenyl)-ethanone

HRID 2219414Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2219414
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([C:13]3[N:14]=[CH:15][N:16]([C:18]4[CH:23]=[CH:22][C:21]([C:24](=[O:26])[CH3:25])=[CH:20][CH:19]=4)[CH:17]=3)=[C:11]([CH2:27][O:28]C)[O:10][N:9]=2)=[CH:4][CH:3]=1.B(Br)(Br)Br>ClCCl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([C:13]3[N:14]=[CH:15][N:16]([C:18]4[CH:23]=[CH:22][C:21]([C:24](=[O:26])[CH3:25])=[CH:20][CH:19]=4)[CH:17]=3)=[C:11]([CH2:27][OH:28])[O:10][N:9]=2)=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 25134Boron tribromideHCID 67420992HCID 67420992, Verbindung

Produkt 1

HCID 674206471-(4-{4-[3-(4-Fluoro-phenyl)-5-hydroxymethyl-isoxazol-4-yl]-imidazol-1-yl}-phenyl)-ethanoneAusbeute 15,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a stirred solution of 1-(4-{4-[3-(4-fluoro-phenyl)-5-methoxymethyl-isoxazol-4-yl]-imidazol-1-yl}-phenyl)-ethanone (239 mg, 0.61 mmol) in dry dichloromethane (4 mL) was added slowly boron tribromide (0.17 mL, 0.3 mmol) at dry ice-acetone bath cooling temperature. After complete addition, the resulting mixture was stirred at −78° C. for 15 min, and −15° C. for 35 min, and then allowed to warm up to room temperature for 20 min. The reaction was quenched with saturated sodium bicarbonate (30 mL). The organic layer was separated, and the aqueous phase was extracted with dichloromethane and ethylacetate. The combined organic extracts were then dried over sodium sulphate and evaporated. Purification by preparative HPLC afforded the title compound (35 mg, 15%) which was obtained as an off-white solid. MS: m/e=378.0 [M+H]+.

Aufarbeitung

  1. temperaturecooling temperature
  2. additionAfter complete addition
  3. wait−15° C. for 35 min
  4. temperatureto warm up to room temperature for 20 min
  5. customThe reaction was quenched with saturated sodium bicarbonate (30 mL)
  6. customThe organic layer was separated
  7. extractionthe aqueous phase was extracted with dichloromethane and ethylacetate
  8. dry with materialThe combined organic extracts were then dried over sodium sulphate
  9. customevaporated
  10. customPurification by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-90c04bd604cd43ea968769424e82795e
Quelldatensatz
uspto-grants-2008_08
Patentnummer
US07414061B2

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