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Sodium Acetate → 2-Bromo-5-(tert-butoxycarbonyl(5-cyano-6-methoxypyridin-2-yl)amino)benzyl acetate

HRID 1260176
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1260176
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([C:16]2[CH:21]=[CH:20][C:19]([C:22]#[N:23])=[C:18]([O:24][CH3:25])[N:17]=2)[C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:4][C:3]=1[CH2:26]Br.[C:28]([O-:31])(=[O:30])[CH3:29].[Na+]>CN(C)C=O>[C:28]([O:31][CH2:26][C:3]1[CH:4]=[C:5]([N:8]([C:9]([O:10][C:11]([CH3:12])([CH3:13])[CH3:14])=[O:15])[C:16]2[CH:21]=[CH:20][C:19]([C:22]#[N:23])=[C:18]([O:24][CH3:25])[N:17]=2)[CH:6]=[CH:7][C:2]=1[Br:1])(=[O:30])[CH3:29]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 517045Sodium AcetateHCID 67305601Tert-butyl 4-bromo-3-(bromomethyl)phenyl(5-cyano-6-methoxypyridin-2-yl)carbamate

Produkt 1

HCID 673059772-Bromo-5-(tert-butoxycarbonyl(5-cyano-6-methoxypyridin-2-yl)amino)benzyl acetateAusbeute 46,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a solution of tert-butyl 4-bromo-3-(bromomethyl)phenyl(5-cyano-6-methoxypyridin-2-yl)carbamate (4.46 g, 8.98 mmol) in N,N-dimethylformamide (60 mL) was added sodium acetate (3.68 g, 44.9 mmol). The reaction was stirred at 50° C. for two hours. The mixture was cooled to room temperature and extracted with ethyl acetate and water in portions. The organic layer of each portion was washed three times with water and brine, and dried over sodium sulfate, and filtered. The portions were combined and the solvent was removed under reduced pressure. The residue was purified by Combiflash to give 2-bromo-5-(tert-butoxycarbonyl(5-cyano-6-methoxypyridin-2-yl)amino)benzyl acetate (1.99 g, 2 steps 46%).

Aufarbeitung

  1. temperatureThe mixture was cooled to room temperature
  2. extractionextracted with ethyl acetate and water in portions
  3. washThe organic layer of each portion was washed three times with water and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customthe solvent was removed under reduced pressure
  7. customThe residue was purified by Combiflash

Quellen und Nachweise

ORD-Eintrag
ord-e70c0b02272947d59d491363562aa4f7
Quelldatensatz
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08470803B2

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