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Potassium Carbonate → 3-Oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-6-carbaldehyde

HRID 1176690
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1176690
[CH:1]([C:9]1[CH:10]=[CH:11][C:12]2[O:13][CH2:14][C:15](=[O:19])[NH:16][C:17]=2[N:18]=1)=CC1C=CC=CC=1.BrC1C=CC2[O:25]CC(=O)NC=2N=1.C1(/C=C/B(O)O)C=CC=CC=1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.O.CCOC(C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[O:19]=[C:15]1[CH2:14][O:13][C:12]2[CH:11]=[CH:10][C:9]([CH:1]=[O:25])=[N:18][C:17]=2[NH:16]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 4

HCID 11430Potassium CarbonateHCID 5702628Styrylboronic acidHCID 218737726-Bromo-2H-pyrido[3,2-B][1,4]oxazin-3(4H)-oneHCID 684438466-Styryl-4H-pyrido[3,2-b][1,4]oxazin-3-one

Produkt 1

HCID 218737373-Oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-6-carbaldehydeAusbeute 43 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

6-Styryl-4H-pyrido[3,2-b][1,4]oxazin-3-one. To a solution of 6-bromo-4H-pyrido[3,2-b][1,4]oxazin-3-one (3.2 g, 14 mmol) in 1,4-dioxane (80 mL) was added trans-2-phenylvinylboronic acid (2.1 g, 14 mmol). After the reaction mixture was degassed with nitrogen, tetrakis(triphenylphosphine)palladium(0) (0.129 g, 0.112 mmol) and a solution of K2CO3 (3.7 g, 27 mmol) in H2O (10.7 mL) were added. The reaction was heated at reflux for 17 h, then cooled to RT, and diluted with EtOAc (300 mL). The organic layer was separated, washed with H2O (300 mL), brine (300 mL), dried (Na2SO4), and concentrated. The solid residue was purified on SiO2 (5-10% EtOAc/CHCl3) to provide 1.5 g (43%) of the title compound as a solid. MS (ESI): exact mass calculated for C15H12N2O2, 252.09; m/z found, 253.2 [M+H]+. 1H NMR (400 MHz, CDCl3): 7.53-7.00 (m, 9H), 4.66 (d, J=6.9, 2H).

Aufarbeitung

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 17 h
  3. customThe organic layer was separated
  4. washwashed with H2O (300 mL), brine (300 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customThe solid residue was purified on SiO2 (5-10% EtOAc/CHCl3)

Quellen und Nachweise

ORD-Eintrag
ord-6e4dd799d36f4c0cbb70ce7654e01064
Quelldatensatz
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07842810B2

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