1,2-Dimethoxyethane → 6-(4-Pyridyl)-4H-benzo[1,4]oxazin-3-one

HRID 495421

Reaktionsgleichung

Reaktionsgleichung von HRID 495421
Br[C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH2:9][C:8](=[O:11])[NH:7][C:6]=2[CH:12]=1.[N:13]1[CH:18]=[CH:17][C:16](B(O)O)=[CH:15][CH:14]=1.C(=O)(O)[O-].[Na+].COCCOC>O>[N:13]1[CH:18]=[CH:17][C:16]([C:2]2[CH:3]=[CH:4][C:5]3[O:10][CH2:9][C:8](=[O:11])[NH:7][C:6]=3[CH:12]=2)=[CH:15][CH:14]=1

Komponenten

6

Edukt 4

HCID 80711,2-DimethoxyethaneHCID 516892Sodium BicarbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 162181426-Bromo-2H-1,4-benzoxazin-3(4H)-one

Produkt 1

HCID 223266866-(4-Pyridyl)-4H-benzo[1,4]oxazin-3-oneAusbeute 43 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 6-bromo-4H-benzo[1,4]oxazin-3-one [N. Mazharuddin et al., Indian J. Chem. 1969, 7, 658] (1.37 g. 6 mmol), pyridine-4-boronic acid (0.72 g, 6 mmol), sodium bicarbonate (1.51 g, 18 mmol), (tetrakis-triphenylphosphine)palladium (0) (348 mg, 0.3 mmol) in water (18 mL), and 1,2-dimethoxyethane (30 mL), was stirred at reflux under an argon atmosphere for 72 h. Reaction mixture was cooled and partitioned between ethyl acetate (100 mL) and water (100 mL). The organic layer was separated and dried (Na2SO4) and evaporated in vacuo to give a brown solid which was purified by chromatography on silica gel (30 g) eluting with 0-5% MeOH in EtOAc to give the title compound (0.58 g, 43%) as a yellow solid.

Aufarbeitung

  1. temperatureat reflux under an argon atmosphere for 72 h
  2. customReaction mixture
  3. temperaturewas cooled
  4. custompartitioned between ethyl acetate (100 mL) and water (100 mL)
  5. customThe organic layer was separated
  6. dry with materialdried (Na2SO4)
  7. customevaporated in vacuo
  8. customto give a brown solid which
  9. customwas purified by chromatography on silica gel (30 g)
  10. washeluting with 0-5% MeOH in EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-9abeb718c33d4565b68635db0f5750c3
Quelldatensatz
uspto-grants-2005_09
Patentnummer
US06939871B2

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