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Boron tribromide → 1-[2-hydroxy-4-(2-hydroxy-5-thiophen3-ylphenyl)-4-methyl-2-trifluoromethylpentyl]-1H-quinolin-4-one

HRID 2106017
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2106017
[OH:1][C:2]([C:32]([F:35])([F:34])[F:33])([CH2:15][C:16]([C:19]1[CH:24]=[C:23]([C:25]2[CH:29]=[CH:28][S:27][CH:26]=2)[CH:22]=[CH:21][C:20]=1[O:30]C)([CH3:18])[CH3:17])[CH2:3][N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7](=[O:14])[CH:6]=[CH:5]1.B(Br)(Br)Br>C(Cl)Cl>[OH:1][C:2]([C:32]([F:35])([F:34])[F:33])([CH2:15][C:16]([C:19]1[CH:24]=[C:23]([C:25]2[CH:29]=[CH:28][S:27][CH:26]=2)[CH:22]=[CH:21][C:20]=1[OH:30])([CH3:18])[CH3:17])[CH2:3][N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7](=[O:14])[CH:6]=[CH:5]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 25134Boron tribromideHCID 578098941-[2-hydroxy-4-(2-methoxy-5-thiophen-3-ylphenyl)-4-methyl-2-trifluoromethylpentyl]-1H-quinolin-4-one

Produkt 1

HCID 578097931-[2-hydroxy-4-(2-hydroxy-5-thiophen3-ylphenyl)-4-methyl-2-trifluoromethylpentyl]-1H-quinolin-4-oneAusbeute 68,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 1-[2-hydroxy-4-(2-methoxy-5-thiophen-3-ylphenyl)-4-methyl-2-trifluoromethylpentyl]-1H-quinolin-4-one (32 mg, 0.06 mmol) in methylene chloride (1 mL) at 0° C. under an argon atmosphere was added BBr3 (0.06 mL, 0.6 mmol). The mixture was warmed to room temperature, stirred 3 hours, cooled to 0° C., stirred 2 days, and quenched with methanol (5 mL). The volatiles were removed in vacuo and the residue diluted with ethyl acetate (10 mL), washed with saturated aqueous sodium bicarbonate (5 mL), and brine (5 mL), and dried over magnesium sulfate. The volatiles were removed in vacuo and the residue purified by reverse phase HPLC to afford 1-[2-hydroxy-4-(2-hydroxy-5-thiophen3-ylphenyl)-4-methyl-2-trifluoromethylpentyl]-1H-quinolin-4-one (20 mg, 68%).

Aufarbeitung

  1. temperaturecooled to 0° C.
  2. stirringstirred 2 days
  3. customquenched with methanol (5 mL)
  4. customThe volatiles were removed in vacuo
  5. additionthe residue diluted with ethyl acetate (10 mL)
  6. washwashed with saturated aqueous sodium bicarbonate (5 mL), and brine (5 mL)
  7. dry with materialdried over magnesium sulfate
  8. customThe volatiles were removed in vacuo
  9. customthe residue purified by reverse phase HPLC

Quellen und Nachweise

ORD-Eintrag
ord-59e523f5dabd409481464abf1f0ae6cb
Quelldatensatz
uspto-grants-2009_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07579469B2

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