Oxazole → Methyl 3-{[ethyl(propyl)amino]carbonyl}-5-(1,3-oxazol-2-yl)benzoate

HRID 349091

Reaktionsgleichung

Reaktionsgleichung von HRID 349091
[O:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.C([Li])CCC.[CH2:11]([N:13]([CH2:27][CH2:28][CH3:29])[C:14]([C:16]1[CH:17]=[C:18]([CH:23]=[C:24](I)[CH:25]=1)[C:19]([O:21][CH3:22])=[O:20])=[O:15])[CH3:12]>O1CCCC1.C(OCC)(=O)C.[Cl-].[Zn+2].[Cl-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[CH2:11]([N:13]([CH2:27][CH2:28][CH3:29])[C:14]([C:16]1[CH:17]=[C:18]([CH:23]=[C:24]([C:2]2[O:1][CH:5]=[CH:4][N:3]=2)[CH:25]=1)[C:19]([O:21][CH3:22])=[O:20])=[O:15])[CH3:12]

Komponenten

8

Edukt 3

HCID 9255OxazoleHCID 21086183Methyl 3-{[ethyl(propyl)amino]carbonyl}-5-iodobenzoateHCID 178418339Butyllithium

Produkt 1

HCID 21086182Methyl 3-{[ethyl(propyl)amino]carbonyl}-5-(1,3-oxazol-2-yl)benzoate

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 3007855ZincchlorideKatalysatorHCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 8028TetrahydrofuranLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a −70° C. stirred solution of oxazole (106 mg, 1.5 mmol) in tetrahydrofuran (4 mL) is added n-butyllithium (1.6 M in hexanes, 1.0 mL, 1.7 mmol). After 30 min, zinc chloride (1 M in diethyl ether, 4.6 mL, 4.6 mmol) is added and the reaction mixture is warmed to 0° C. for 1 h. To this mixture is added a solution of methyl 3-{[ethyl(propyl)amino]carbonyl}-5-iodobenzoate (535 mg, 1.45 mmol) in anhydrous tetrahydrofuran (1.8 mL) followed by palladium(0) tetrakis(triphenylphosphine) (120 mg, 0.10 mmol). The reaction mixture is heated at reflux for 2 h. The reaction mixture is cooled, diluted with ethyl acetate, washed with water, and saturated sodium chloride, dried (sodium sulfate), filtered, and concentrated under reduced pressure. Purification by flash column chromatography (silica gel, 60% ethyl acetate/hexane) provides the title compound. ESI MS m/z 317.1 [M+H]+.

Aufarbeitung

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux for 2 h
  3. temperatureThe reaction mixture is cooled
  4. washwashed with water, and saturated sodium chloride
  5. dry with materialdried (sodium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customPurification by flash column chromatography (silica gel, 60% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-e5dad322168c4dca91b45695693fad3b
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07176242B2

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