Cesium carbonate → Methyl 2-([(2,4-difluorophenyl)methyl]oxy}-5-(4-morpholinylcarbonyl)benzoate
Reaktionsgleichung
[OH:1][C:2]1[CH:11]=[CH:10][C:9]([C:12]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)=[O:13])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:27][C:28]1[CH:33]=[CH:32][C:31]([F:34])=[CH:30][C:29]=1[F:35]>CC(C)=O>[F:35][C:29]1[CH:30]=[C:31]([F:34])[CH:32]=[CH:33][C:28]=1[CH2:27][O:1][C:2]1[CH:11]=[CH:10][C:9]([C:12]([N:14]2[CH2:15][CH2:16][O:17][CH2:18][CH2:19]2)=[O:13])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 50 °C
Versuchsvorschrift
To a stirred solution of methyl 2-hydroxy-5-(4-morpholinylcarbonyl)benzoate (may be prepared as described in Description 108, 270 mg, 1.02 mmol) in acetone (3 ml) was added cesium carbonate (663 mg, 2.04 mmol) and 1-(bromomethyl)-2,4-difluorobenzene (0.17 ml, 1.32 mmol). The mixture was heated at 50° C. for 2 hours, cooled and the solvent removed in vacuo. The residue was partitioned between water (5 ml) and ethyl acetate (10 ml). The organic layer was dried (MgSO4) and the solvent removed in vacuo to give a residue. Purification by column chromatography (silicon, 4:1 ethyl acetate/cyclohexane) yielded the title compound as a yellow gum. 100 mg.
Aufarbeitung
- temperaturecooled
- customthe solvent removed in vacuo
- customThe residue was partitioned between water (5 ml) and ethyl acetate (10 ml)
- dry with materialThe organic layer was dried (MgSO4)
- customthe solvent removed in vacuo
- customto give a residue
- customPurification by column chromatography (silicon, 4:1 ethyl acetate/cyclohexane)
Quellen und Nachweise
- ORD-Eintrag
- ord-805aab774ace4f6bb78021d601140838
- Quelldatensatz
- uspto-grants-2014_07
- Patentnummer
- US08778939B2
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