Sodium Bicarbonate → N-(4-(2-((t-butyl(dimethyl)silyl)oxy)-4-hydroxybutanoyl)-3-fluorophenyl)pyridine-2-carboxamide

HRID 13383

Reaktionsgleichung

Reaktionsgleichung von HRID 13383
C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)=[O:15])=[CH:9][C:8]=1[F:22].[Si:23]([O:30][CH:31]1[CH2:35][CH2:34][O:33][C:32]1=[O:36])([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24].C(=O)(O)[O-].[Na+]>O1CCCC1>[Si:23]([O:30][CH:31]([CH2:35][CH2:34][OH:33])[C:32]([C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)=[O:15])=[CH:9][C:8]=1[F:22])=[O:36])([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24]

Komponenten

6

Edukt 4

HCID 516892Sodium BicarbonateHCID 50462413-(tert-butyldimethylsilyloxy)dihydrofuran-2(3H)-oneHCID 23145244N-(4-bromo-3-fluorophenyl)pyridine-2-carboxamideHCID 178418339Butyllithium

Produkt 1

HCID 67482856N-(4-(2-((t-butyl(dimethyl)silyl)oxy)-4-hydroxybutanoyl)-3-fluorophenyl)pyridine-2-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

3.1 ml of n-butyl lithium (2.66 M hexane solution) was dropwise added to a tetrahydrofuran (100 ml) solution of 1.1 g of N-(4-bromo-3-fluorophenyl)pyridine-2-carboxamide at −78° C., and the reaction liquid was stirred at the same temperature for 15 minutes. 1.21 g of 3-((t-butyl(dimethyl)silyl)oxy)dihydrofuran-2 (3H)-one was added to the reaction liquid, and the reaction liquid was stirred at the same temperature for 1 hour. Aqueous saturated sodium bicarbonate solution was added to the reaction liquid at the same temperature, then heated up to room temperature and extracted with ethyl acetate. The organic layer was dried with anhydrous sodium sulfate, the solvent was evaporated away under reduced pressure, and the resulting residue was purified through silica gel column chromatography (developing solvent: chloroform/methanol=100/1) to obtain the entitled compound as a colorless oily substance.

Aufarbeitung

  1. customthe reaction liquid
  2. customthe reaction liquid
  3. stirringwas stirred at the same temperature for 1 hour
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  6. customthe solvent was evaporated away under reduced pressure
  7. customthe resulting residue was purified through silica gel column chromatography (developing solvent: chloroform/methanol=100/1)
  8. customto obtain the entitled compound as a colorless oily substance

Quellen und Nachweise

ORD-Eintrag
ord-5792d20b11a24431869bed1f57a12458
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728025B2

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