Sodium Carbonate → t-Butyl 2-(2-fluoro-5-nitro-phenyl)-pyrrole-1-carboxylate

HRID 13274

Reaktionsgleichung

Reaktionsgleichung von HRID 13274
C(=O)([O-])[O-].[Na+].[Na+].Br[C:8]1[CH:9]=[C:10]([N+:15]([O-:17])=[O:16])[CH:11]=[CH:12][C:13]=1[F:14].[C:18]([O:22][C:23]([N:25]1[CH:29]=[CH:28][CH:27]=[C:26]1B(O)O)=[O:24])([CH3:21])([CH3:20])[CH3:19].C(=O)(O)[O-].[Na+]>C(COC)OC.O>[F:14][C:13]1[CH:12]=[CH:11][C:10]([N+:15]([O-:17])=[O:16])=[CH:9][C:8]=1[C:26]1[N:25]([C:23]([O:22][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:24])[CH:29]=[CH:28][CH:27]=1

Komponenten

7

Edukt 4

HCID 10340Sodium CarbonateHCID 696992-Bromo-1-fluoro-4-nitrobenzeneHCID 516892Sodium BicarbonateHCID 27343211-(tert-Butoxycarbonyl)-2-pyrroleboronic Acid

Produkt 1

HCID 23145764t-Butyl 2-(2-fluoro-5-nitro-phenyl)-pyrrole-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

1.1 g of tetrakis-triphenylphosphine palladium and 4.2 g of sodium carbonate were added to a solution of 4.3 g of 3-bromo-4-fluoro-nitrobenzene and 5.0 g of 1-(t-butoxycarbonyl)pyrrole-2-boronic acid in a mixture of 130 ml of dimethoxyethane and 22 ml of water, and the reaction liquid was heated overnight under reflux. Aqueous saturated sodium bicarbonate was added to the reaction liquid, and this was extracted with ethyl acetate. The organic layer was washed with water and saturated saline in order, and 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: hexane/ethyl acetate=20/1) to obtain the entitled compound as a yellow oily substance.

Aufarbeitung

  1. customthe reaction liquid
  2. temperaturewas heated overnight
  3. temperatureunder reflux
  4. extractionthis was extracted with ethyl acetate
  5. washThe organic layer was washed with water and saturated saline in order
  6. dry with materialdried with anhydrous sodium sulfate
  7. customThe solvent was evaporated away under reduced pressure
  8. customthe resulting residue was purified through silica gel column chromatography (developing solvent: hexane/ethyl acetate=20/1)
  9. customto obtain the entitled compound as a yellow oily substance

Quellen und Nachweise

ORD-Eintrag
ord-5b2c7caafde048c49c5bbc8275c188f1
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728025B2

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