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Sodium bis(trimethylsilyl)amide → 3-methyl-2-oxazol-2-yl-1-phenyl-1H-[1,8]naphthyridin-4-one

HRID 1887785
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1887785
[C:1]1([NH:7][C:8]2[C:13]([C:14](=[O:17])[CH2:15][CH3:16])=[CH:12][CH:11]=[CH:10][N:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[O:28]1[CH:32]=[CH:31][N:30]=[C:29]1[C:33](Cl)=O>C1COCC1.CN(C=O)C.O>[CH3:16][C:15]1[C:14](=[O:17])[C:13]2[C:8](=[N:9][CH:10]=[CH:11][CH:12]=2)[N:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:33]=1[C:29]1[O:28][CH:32]=[CH:31][N:30]=1
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Komponenten

7

Edukt 3

HCID 2724254Sodium bis(trimethylsilyl)amideHCID 22646749Oxazole-2-carbonyl chlorideHCID 712088531-(2-Phenylamino-pyridin-3-yl)-propan-1-one

Produkt 1

HCID 712082443-methyl-2-oxazol-2-yl-1-phenyl-1H-[1,8]naphthyridin-4-oneAusbeute 20,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6228Dimethylformamide
Katalysator
HCID 962WaterLösungsmittel
HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

A solution of 1-(2-phenylamino-pyridin-3-yl)-propan-1-one (2.0 g, 8.84 mmol) in THF (17.7 mL) at 25° C. was treated with sodium bis(trimethylsilyl)amide (1.0 M in THF) (22.1 mL, 22.1 mmol). The resulting red solution was then treated with a mixture of oxazole-2-carbonyl chloride (1.51 g, 11.5 mmol) in THF (8 mL) and 10 drops of DMF. The reaction was then stirred at 25° C. overnight. The reaction was diluted with water (50 mL) and was then extracted into ethyl acetate (3×50 mL). The organics were dried over sodium sulfate, filtered and concentrated in vacuo. The resulting residue was absorbed onto silica and dried under high vacuum. Flash chromatography (25 g, 25%-75% ethyl acetate-hexanes) afforded 3-methyl-2-oxazol-2-yl-1-phenyl-1H-[1,8]naphthyridin-4-one (540 mg, 20.1%) as a light yellow solid.

Aufarbeitung

  1. extractionwas then extracted into ethyl acetate (3×50 mL)
  2. dry with materialThe organics were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe resulting residue was absorbed onto silica
  6. customdried under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-56fa0c510c3b41fe92b5d5904b4ff22e
Quelldatensatz
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08501732B2

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