Sodium bis(trimethylsilyl)amide → 7-chloro-3-methyl-2-oxazol-2-yl-1-phenyl-1H-quinolin-4-one

HRID 1887781

Reaktionsgleichung

Reaktionsgleichung von HRID 1887781
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:11])[CH2:9][CH3:10])=[C:4]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:3]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[O:29]1[CH:33]=[CH:32][N:31]=[C:30]1[C:34](Cl)=O>C1COCC1.CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:5]([C:8](=[O:11])[C:9]([CH3:10])=[C:34]([C:30]3[O:29][CH:33]=[CH:32][N:31]=3)[N:12]2[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[CH:6][CH:7]=1

Komponenten

6

Edukt 3

HCID 2724254Sodium bis(trimethylsilyl)amideHCID 22646749Oxazole-2-carbonyl chlorideHCID 708166141-(4-Chloro-2-phenylamino-phenyl)-propan-1-one

Produkt 1

HCID 712081907-chloro-3-methyl-2-oxazol-2-yl-1-phenyl-1H-quinolin-4-oneAusbeute 23,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideKatalysatorHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

In a 25 mL round-bottomed flask, 1-(4-chloro-2-phenylamino-phenyl)-propan-1-one (522 mg, 2.01 mmol) was combined with THF (4 mL) to give a yellow solution. Sodium bis(trimethylsilyl)amide (1.0 M in THF) (5.02 mL, 5.02 mmol) was added slowly dropwise, resulting in a dark red solution. A mixture of oxazole-2-carbonyl chloride (344 mg, 2.61 mmol) in THF (8 mL) and 8 drops of DMF were added to the reaction mixture. The resulting mixture was stirred at room temperature for 5 hr. The reaction mixture was quenched by the addition of water and the aqueous layer was extracted with ethyl acetate. The organic phase was dried (MgSO4), filtered, then concentrated to afford a yellow oil. The crude material was purified by flash chromatography (silica gel, 80 g, 25-65% ethyl acetate in hexanes) to give 7-chloro-3-methyl-2-oxazol-2-yl-1-phenyl-1H-quinolin-4-one (160 mg, 23.6%) as a yellowish solid. MS calcd. for C19H13ClN2O2 [(M+H)+] 337, obsd. 337.

Aufarbeitung

  1. customto give a yellow solution
  2. customresulting in a dark red solution
  3. additionwere added to the reaction mixture
  4. customThe reaction mixture was quenched by the addition of water
  5. extractionthe aqueous layer was extracted with ethyl acetate
  6. dry with materialThe organic phase was dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto afford a yellow oil
  10. customThe crude material was purified by flash chromatography (silica gel, 80 g, 25-65% ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-927e09f4728c4fddaa2a5b8fde1b9c2d
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08501732B2

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