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Ethyl Acetate → tert-butyl N-(7-bromo-2-methoxypyrazolo[1,5-a]pyridin-3-yl)-N-cyclopropylmethylcarbamate

HRID 347843
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 347843
[H-].[Na+].[Br:3][C:4]1[N:9]2[N:10]=[C:11]([O:21][CH3:22])[C:12]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[C:8]2[CH:7]=[CH:6][CH:5]=1.Br[CH2:24][CH:25]1[CH2:27][CH2:26]1.C(OCC)(=O)C>CN(C)C=O>[Br:3][C:4]1[N:9]2[N:10]=[C:11]([O:21][CH3:22])[C:12]([N:13]([CH2:24][CH:25]3[CH2:27][CH2:26]3)[C:14](=[O:20])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])=[C:8]2[CH:7]=[CH:6][CH:5]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 81503BromomethylcyclopropaneHCID 21984642tert-butyl N-(7-bromo-2-methoxypyrazolo[1,5-a]pyridin-3-yl)carbamate

Produkt 1

HCID 21084188tert-butyl N-(7-bromo-2-methoxypyrazolo[1,5-a]pyridin-3-yl)-N-cyclopropylmethylcarbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel

Versuchsvorschrift

Sodium hydride (60% in oil; 24.6 mg) was added to a solution of tert-butyl N-(7-bromo-2-methoxypyrazolo[1,5-a]pyridin-3-yl)carbamate (140 mg) in N,N-dimethylformamide (10 mL) at room temperature and the reaction mixture was stirred for 30 minutes. (Bromomethyl)cyclopropane (0.06 mL) was added thereto at the same temperature, and the reaction mixture was stirred for 1 hour at 60° C. After completion of the reaction, the reaction mixture was gradually added to ice, extraction was performed with ethyl acetate, the organic extract was washed with water and brine, dried over anhydrous magnesium sulfate and filtered, and the solvent was evaporated under reduced pressure to afford a crude product of tert-butyl N-(7-bromo-2-methoxypyrazolo[1,5-a]pyridin-3-yl)-N-cyclopropylmethylcarbamate.

Aufarbeitung

  1. stirringat the same temperature, and the reaction mixture was stirred for 1 hour at 60° C
  2. customAfter completion of the reaction
  3. additionthe reaction mixture was gradually added to ice, extraction
  4. extractionthe organic extract
  5. washwas washed with water and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customthe solvent was evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-d624d13d299b414d882b057397a26ea0
Quelldatensatz
uspto-grants-2007_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07176216B2

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