Imidazole → 3-((5-Bromo-2-methoxyphenyl)(tert-butyldimethylsilyloxy)methyl)-2,6-difluoropyridine

HRID 335902Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 335902
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:18][CH3:19])=[C:6]([CH:8]([C:10]2[C:11]([F:17])=[N:12][C:13]([F:16])=[CH:14][CH:15]=2)[OH:9])[CH:7]=1.N1C=CN=C1.[C:25]([Si:29](Cl)([CH3:31])[CH3:30])([CH3:28])([CH3:27])[CH3:26].O>CN(C=O)C.C(OCC)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:18][CH3:19])=[C:6]([CH:8]([O:9][Si:29]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:31])[CH3:30])[C:10]2[C:11]([F:17])=[N:12][C:13]([F:16])=[CH:14][CH:15]=2)[CH:7]=1

Komponenten

7

Edukt 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 67383458(5-Bromo-2-methoxyphenyl)(2,6-difluoropyridin-3-yl)methanol

Produkt 1

HCID 673831653-((5-Bromo-2-methoxyphenyl)(tert-butyldimethylsilyloxy)methyl)-2,6-difluoropyridine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

(5-Bromo-2-methoxyphenyl)(2,6-difluoropyridin-3-yl)methanol (13.77 g, 41.7 mmol) and imidazole (3.41 g, 50.1 mmol) were dissolved in dry DMF (20 mL) under nitrogen. t-Butyl(chloro)dimethylsilane (6.92 g, 45.9 mmol) was added and the solution heated to 70° C. After 1 hour the mixture was cooled to RT. Water (200 mL) and diethyl ether (200 mL) were added and the phases mixed and separated. The organic was washed with water (200 mL) one more time then dried with magnesium sulfate and evaporated to dryness under reduced pressure. Purification using silica chromatography (hexane to 1:1 DCM: hexane gradient) gave 3-((5-bromo-2-methoxyphenyl)(tert-butyldimethylsilyloxy)methyl)-2,6-difluoropyridine as a thick oil that solidified on standing.

Aufarbeitung

  1. temperatureAfter 1 hour the mixture was cooled to RT
  2. additionthe phases mixed
  3. customseparated
  4. washThe organic was washed with water (200 mL) one more time
  5. dry with materialthen dried with magnesium sulfate
  6. customevaporated to dryness under reduced pressure
  7. customPurification

Quellen und Nachweise

ORD-Eintrag
ord-177acd573d094f4ead0f1d968a405d05
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08883782B2

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