Hydrochloric Acid → 1-{4-[4-(5-Acetyl-2-morpholin-4-yl-benzoyl)-piperazin-1-yl]-3-fluoro-phenyl}-ethanone

HRID 736191

Reaktionsgleichung

Reaktionsgleichung von HRID 736191
Br[C:2]1[CH:3]=[CH:4][C:5]([N:26]2[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)=[C:6]([CH:25]=1)[C:7]([N:9]1[CH2:14][CH2:13][N:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21](=[O:23])[CH3:22])=[CH:17][C:16]=2[F:24])[CH2:11][CH2:10]1)=[O:8].C([Sn](CCCC)(CCCC)[C:37]([O:39]CC)=[CH2:38])CCC.Cl>C1(C)C=CC=CC=1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:37]([C:2]1[CH:3]=[CH:4][C:5]([N:26]2[CH2:27][CH2:28][O:29][CH2:30][CH2:31]2)=[C:6]([CH:25]=1)[C:7]([N:9]1[CH2:10][CH2:11][N:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21](=[O:23])[CH3:22])=[CH:17][C:16]=2[F:24])[CH2:13][CH2:14]1)=[O:8])(=[O:39])[CH3:38]

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 445805131-(4-(4-(5-Bromo-2-morpholinobenzoyl)piperazin-1-yl)-3-fluorophenyl)ethanone

Produkt 1

HCID 597935521-{4-[4-(5-Acetyl-2-morpholin-4-yl-benzoyl)-piperazin-1-yl]-3-fluoro-phenyl}-ethanoneAusbeute 10 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a suspension of 1-{4-[4-(5-Bromo-2-morpholin-4-yl-benzoyl)-piperazin-1-yl]-3-fluoro-phenyl}-ethanone (160 mg, 0.33 mmol) in toluene (2 ml) were added PdCl2(PPh3)2 (5 mg, 0.0065 mmol) and tributyl(1-ethoxyvinyl) tin (125 ul, 0.36 mmol). The mixture was heated to 100° C. for 6 hours. The mixture was cooled in an ice bath and 2N HCl (0.55 ml) was added. The mixture was stirred at room temperature overnight. The mixture was filtered. The organic layer was separated and 10% aqueous KF solution was added. The mixture was stirred at room temperature for 3 hours and filtered. The organic layer was dried over Na2SO4, filtered and the solvent was removed in vacuo. The crude gum was chromatographed on silica gel, eluent: heptane/ethylacetate 0%-50% (10 minutes) to provide the title compound (15 mg, 10%) as a white solid MS (m/e): 454.2 (M+H, 100%).

Aufarbeitung

  1. temperatureThe mixture was cooled in an ice bath
  2. filtrationThe mixture was filtered
  3. customThe organic layer was separated
  4. addition10% aqueous KF solution was added
  5. stirringThe mixture was stirred at room temperature for 3 hours
  6. filtrationfiltered
  7. dry with materialThe organic layer was dried over Na2SO4
  8. filtrationfiltered
  9. customthe solvent was removed in vacuo
  10. customThe crude gum was chromatographed on silica gel, eluent

Quellen und Nachweise

ORD-Eintrag
ord-d956c20305fc4f61a652155aeb5955c5
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07595314B2

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