Sodium hydride → 4-(4-Bromo-3-fluorophenoxy)-2-methylpyridine 1-oxide

HRID 404702

Reaktionsgleichung

Reaktionsgleichung von HRID 404702
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[F:9].[H-].[Na+].[N+]([C:15]1[CH:16]=[C:17]([CH3:22])[N+:18]([O-:21])=[CH:19][CH:20]=1)([O-])=O>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:15]2[CH:20]=[CH:19][N+:18]([O-:21])=[C:17]([CH3:22])[CH:16]=2)=[CH:4][C:3]=1[F:9]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 95291Pyridine, 2-methyl-4-nitro-, 1-oxideHCID 27791534-Bromo-3-fluorophenol

Produkt 1

HCID 592873124-(4-Bromo-3-fluorophenoxy)-2-methylpyridine 1-oxide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
180 °C

Versuchsvorschrift

4-Bromo-3-fluorophenol (0.5 g, 2.61 mmol) was added to a solution of sodium hydride (0.115 g, 2.90 mmol) in DMF (5 ml). After stiffing for 10 minutes 4-nitro-2-picoline N-oxide (0.37 g, 2.41 mmol) was added. The reaction mixture was heated at 180° C. for 1 hour under microwave irradiation. After cooling to room temperature the mixture was filtered through diatomaceous earth and this was thoroughly washed with EtOAc. The filtrate was washed with water (2×25 ml), the organic fraction was dried (Na2SO4) and the solvent evaporated in vacuo. The crude product was purified by column chromatography (silica gel; 0-3% methanol/DCM as eluent). The desired fractions were collected and evaporated in vacuo to yield intermediate D12 (0.33 g, 49%).

Aufarbeitung

  1. temperatureAfter cooling to room temperature the mixture
  2. filtrationwas filtered through diatomaceous earth
  3. washthis was thoroughly washed with EtOAc
  4. washThe filtrate was washed with water (2×25 ml)
  5. dry with materialthe organic fraction was dried (Na2SO4)
  6. customthe solvent evaporated in vacuo
  7. customThe crude product was purified by column chromatography (silica gel; 0-3% methanol/DCM as eluent)
  8. customThe desired fractions were collected
  9. customevaporated in vacuo
  10. customto yield intermediate D12 (0.33 g, 49%)

Quellen und Nachweise

ORD-Eintrag
ord-1dcfdd3f566349dbb75c98d9510b130b
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08748621B2

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