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Lithium hexamethyldisilazane → HCID 59547928, Verbindung

HRID 1946419
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1946419
[F:1][C:2]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[C:3]=1[C:4]([NH:6][C:7]1[CH:11]=[CH:10][NH:9][N:8]=1)=[O:5].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[Br:27][C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([O:34][C:35]([F:38])([F:37])[F:36])[C:29]=1[CH2:39]Br>C1COCC1>[Br:27][C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([O:34][C:35]([F:36])([F:37])[F:38])[C:29]=1[CH2:39][N:9]1[CH:10]=[CH:11][C:7]([NH:6][C:4](=[O:5])[C:3]2[C:12]([F:16])=[CH:13][CH:14]=[CH:15][C:2]=2[F:1])=[N:8]1
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Komponenten

5

Edukt 3

HCID 2733832Lithium hexamethyldisilazaneHCID 667709031-Bromo-2-(bromomethyl)-3-[(trifluoromethyl)oxy]benzeneHCID 178522346HCID 178522346, Verbindung2×

Produkt 1

HCID 59547928HCID 59547928, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

2,6-difluoro-N-1H-pyrazol-3-ylbenzamide (for a preparation see Intermediate 9)(45 mg, 0.202 mmol) in dry THF (3.0 ml) was stirred under nitrogen at ambient temperature, 1.0 M lithium bis(trimethylsilyl)amide (0.20 ml, 0.20 mmol) was added dropwise and the solution stirred for approximately 90 min then 1-bromo-2-(bromomethyl)-3-[(trifluoromethyl)oxy]benzene (67.3 mg, 1 equiv) in THF (2 ml) was added. The solution was stirred for 5 h then left to stand overnight. The solvent was removed using a stream of nitrogen. To the residue was added aqueous sodium bicarbonate and the mixture was extracted with chloroform three times. The combined organic extracts were filtered through a hydrophobic frit and the filtrate was concentrated in vacuo. The residue was purified by MDAP (Method B). The appropriate fractions were combined and evaporated in vacuo to give the title compound as a white solid (80.6 mg) after drying at high vacuum at 45° C.; LCMS: (System 4) MH+=476, tRET=3.01 min.

Aufarbeitung

  1. stirringthe solution stirred for approximately 90 min
  2. stirringThe solution was stirred for 5 h
  3. waitthen left
  4. customThe solvent was removed
  5. additionTo the residue was added aqueous sodium bicarbonate
  6. extractionthe mixture was extracted with chloroform three times
  7. filtrationThe combined organic extracts were filtered through a hydrophobic frit
  8. concentrationthe filtrate was concentrated in vacuo
  9. customThe residue was purified by MDAP (Method B)
  10. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-59e2e126b90a4cf498dd53d83053f117
Quelldatensatz
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08399436B2

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