Sodium Carbonate → (2,3-Dihydrobenzo[1,4]oxazin-4-yl)[3-(4-fluoro-2-(trifluoromethyl)phenyl)-2,5-dihydropyrrol-1-yl]methanone

HRID 551826

Reaktionsgleichung

Reaktionsgleichung von HRID 551826
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]([C:11]([N:13]2[CH2:17][CH:16]=[C:15](B3OC(C)(C)C(C)(C)O3)[CH2:14]2)=[O:12])[CH2:3][CH2:2]1.Br[C:28]1[CH:33]=[CH:32][C:31]([F:34])=[CH:30][C:29]=1[C:35]([F:38])([F:37])[F:36].C(=O)([O-])[O-].[Na+].[Na+]>O.COCCOC>[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]([C:11]([N:13]2[CH2:17][CH:16]=[C:15]([C:28]3[CH:33]=[CH:32][C:31]([F:34])=[CH:30][C:29]=3[C:35]([F:36])([F:38])[F:37])[CH2:14]2)=[O:12])[CH2:3][CH2:2]1

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 5209832-Bromo-5-fluorobenzotrifluorideHCID 67187569(2,3-Dihydrobenzo[1,4]oxazin-4-yl)[3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-2,5-dihydropyrrol-1-yl]methanone

Produkt 1

HCID 67187504(2,3-Dihydrobenzo[1,4]oxazin-4-yl)[3-(4-fluoro-2-(trifluoromethyl)phenyl)-2,5-dihydropyrrol-1-yl]methanoneAusbeute 70,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

0.4 g of (2,3-dihydrobenzo[1,4]oxazin-4-yl)[3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-2,5-dihydropyrrol-1-yl]methanone, 0.4 g of 1-bromo-4-fluoro-2-(trifluoromethyl)benzene, 1.4 ml of a 2N solution of sodium carbonate in water and 15 ml of ethylene glycol dimethyl ether are placed in a 100 ml three-necked flask equipped with a magnetic stirrer and placed under an inert atmosphere. The reaction mixture is degassed with nitrogen for 30 minutes and then the reaction mixture is heated at reflux for 14 h. After filtering and concentrating to dryness, the crude reaction product obtained is chromatographed on silica gel, elution being carried out with a gradient of ethyl acetate in dichloromethane varying from 0% to 10%. 0.31 g of (2,3-dihydrobenzo[1,4]oxazin-4-yl)[3-(4-fluoro-2-(trifluoromethyl)phenyl)-2,5-dihydropyrrol-1-yl]methanone is obtained.

Aufarbeitung

  1. customequipped with a magnetic stirrer
  2. customThe reaction mixture is degassed with nitrogen for 30 minutes
  3. temperaturethe reaction mixture is heated
  4. temperatureat reflux for 14 h
  5. filtrationAfter filtering
  6. concentrationconcentrating to dryness
  7. customthe crude reaction product
  8. customobtained
  9. customis chromatographed on silica gel, elution

Quellen und Nachweise

ORD-Eintrag
ord-21d0623101a14257861d5146c451eddd
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07947834B2

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