Potassium Carbonate → 2-(6-bromo-2-oxo-7-phenyl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-1-yl)acetonitrile
Reaktionsgleichung
[Br:1][C:2]1[C:3]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:4][C:5]2[NH:10][C:9](=[O:11])[CH2:8][O:7][C:6]=2[N:12]=1.Br[CH2:20][C:21]#[N:22].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[Br:1][C:2]1[C:3]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:4][C:5]2[N:10]([CH2:20][C:21]#[N:22])[C:9](=[O:11])[CH2:8][O:7][C:6]=2[N:12]=1Komponenten
6
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 50 °C
Versuchsvorschrift
A mixture of 6-bromo-7-phenyl-1H-pyrido[2,3-b][1,4]oxazin-2(3H)-one (0.4 g, 1.311 mmol), 2-bromoacetonitrile (0.472 g, 3.93 mmol) and potassium carbonate (0.544 g, 3.93 mmol) in DMF (4 ml) was stirred at 50° C. for 2 h. The reaction mixture was diluted with water (20 ml) and extracted with dichloromethane (3×20 ml). The combined organic phase was washed with water, brine, dried over sodium sulfate and concentrated to give crude product which was purified by column chromatography (biotage 25 g) eluted with 0-50% ethyl acetate/cyclohexane to afford product (0.19 g) 1H NMR (500 MHz, CDCl3) 7.45-7.50 (m, 3H), 7.4-7.43 (m, 2H), 7.31 (s, 1H), 4.93 (s, 2H), 4.83 (s, 2H).
Aufarbeitung
- extractionextracted with dichloromethane (3×20 ml)
- washThe combined organic phase was washed with water, brine
- dry with materialdried over sodium sulfate
- concentrationconcentrated
- customto give crude product which
- customwas purified by column chromatography (biotage 25 g)
- washeluted with 0-50% ethyl acetate/cyclohexane
Quellen und Nachweise
- ORD-Eintrag
- ord-61c0b0cbab7e41c791341c5d515ea3fb
- Quelldatensatz
- uspto-grants-2015_12
- Patentnummer
- US09221838B2
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