Phthalimide → 2-((6-Bromopyridin-2-yl)methyl)isoindoline-1,3-dione

HRID 29259

Reaktionsgleichung

Reaktionsgleichung von HRID 29259
[Br:1][C:2]1[N:7]=[C:6]([CH2:8]O)[CH:5]=[CH:4][CH:3]=1.[C:10]1(=[O:20])[NH:14][C:13](=[O:15])[C:12]2=[CH:16][CH:17]=[CH:18][CH:19]=[C:11]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1CCN(C(N=NC(N2CCCCC2)=O)=O)CC1>C1COCC1>[Br:1][C:2]1[N:7]=[C:6]([CH2:8][N:14]2[C:10](=[O:20])[C:11]3[C:12](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:13]2=[O:15])[CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 3517811(6-Bromopyridin-2-yl)methanol

Produkt 1

HCID 221764462-((6-Bromopyridin-2-yl)methyl)isoindoline-1,3-dioneAusbeute 80,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

(6-Bromo-pyridin-2-yl)-methanol (2949 mg, 15.68 mmol), phthalimide (3000 mg, 20.39 mmol), triphenylphosphine (5348 mg, 20.39 mmol) and 1,1-(azodicarbonyl)-dipiperidine) 5144, 20.39 mmol) were dissolved in THF (150 mL) and stirred at room temperature for 4 h. The reaction mixture was cooled to 0° C. and the resulting precipitate was removed via filtration. A saturated aqueous sodium bicarbonate solution was added to the filtrate and the solution was extracted several times with ethyl acetate. The combined organic extracts were dried over magnesium sulfate and condensed under reduced pressure. The crude residue was purified by column chromatography with a gradient of 10 to 75% AcOEt/hexanes to give 2-(6-Bromo-pyridin-2-ylmethyl)-isoindole-1,3-dione as a white solid (4000 mg, 80%) MS ES (MH+317.2/319.1).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. customthe resulting precipitate was removed via filtration
  3. additionA saturated aqueous sodium bicarbonate solution was added to the filtrate
  4. extractionthe solution was extracted several times with ethyl acetate
  5. dry with materialThe combined organic extracts were dried over magnesium sulfate and condensed under reduced pressure
  6. customThe crude residue was purified by column chromatography with a gradient of 10 to 75% AcOEt/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-9df312f38a2d4e13b15522a5728d118a
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07420066B2

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