Benzyl Bromide → methyl 1-benzyl-2-oxo-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine-7-carboxylate

HRID 2421884Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2421884
[O:1]=[C:2]1[CH2:7][O:6][C:5]2[N:8]=[CH:9][C:10]([C:12]([O:14][CH3:15])=[O:13])=[CH:11][C:4]=2[NH:3]1.C(=O)([O-])[O-].[K+].[K+].[CH2:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CN(C=O)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CCOC(C)=O.C(=O)(O)[O-].[Na+]>[CH2:22]([N:3]1[C:2](=[O:1])[CH2:7][O:6][C:5]2[N:8]=[CH:9][C:10]([C:12]([O:14][CH3:15])=[O:13])=[CH:11][C:4]1=2)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Komponenten

8

Edukt 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 57896640Methyl 2-oxo-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine-7-carboxylate

Produkt 1

HCID 57896764methyl 1-benzyl-2-oxo-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine-7-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 67553Tetrabutylammonium IodideKatalysatorHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Methyl 2 oxo-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine-7-carboxylate (50 mg, 240 μmol) was dissolved in DMF (0.5 mL) in a 2 mL microwave vial containing a magnetic stirrer bar. Potassium carbonate (100 mg, 720 μmol) was added to the vial followed by benzyl bromide (62 mg, 360 μmol) and tetrabutylammonium iodide (10 mg, 27 μmol). The vial was capped and was heated to 100° C. by microwave irradiation for 5 minutes. The reaction mixture was diluted with EtOAc (3 mL) and of saturated aqueous sodium bicarbonate (3 mL). The organic layer was removed and the aqueous layer was extracted with 2 mL of EtOAc. The organic layers were combined, dried over anhydrous Na2SO4 filtered and evaporated. This yielded 70 mg of a yellow oil which was used without further purification. LCMS (+ESI) m/z=299.1 [M+H]+.

Aufarbeitung

  1. additioncontaining a magnetic stirrer bar
  2. customThe vial was capped
  3. customThe organic layer was removed
  4. extractionthe aqueous layer was extracted with 2 mL of EtOAc
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. customThis yielded 70 mg of a yellow oil which was used without further purification

Quellen und Nachweise

ORD-Eintrag
ord-9277d09840f94170be7ed558d64870a1
Quelldatensatz
uspto-grants-2011_06
Patentnummer
US07960377B2

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