Bromobenzene → [4-(5-Methyl-3-phenyl-isoxazol-4-yl)-pyrimidin-2-yl]-phenyl-amine

HRID 1375631Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1375631
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[C:13]1[CH:18]=[CH:17][N:16]=[C:15]([NH2:19])[N:14]=1.Br[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C(OCC)(=O)C.[Pd].[Pd].C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1>[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:3]=1[C:13]1[CH:18]=[CH:17][N:16]=[C:15]([NH:19][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:14]=1

Komponenten

8

Edukt 4

HCID 7961BromobenzeneHCID 634876Binap, (A+-)-HCID 27457214-(5-Methyl-3-phenylisoxazol-4-yl)pyrimidin-2-amineHCID 23676156Sodium t-butoxide

Produkt 1

HCID 9949334[4-(5-Methyl-3-phenyl-isoxazol-4-yl)-pyrimidin-2-yl]-phenyl-amineAusbeute 36,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 9832798Tris(dibenzylideneacetone) dipalladiumKatalysatorHCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 50 mg (0.2 mmol) of 4-(5-methyl-3-phenyl-isoxazole-4-yl)-pyrimidin-2-ylamine in 1 mL of toluene was added successively 63 μL (0.6 mmol) of bromobenzene, 10 mg of tris(dibenzylideneacetone) dipalladium, 10 mg of BINAP and 39 mg (0.4 mmol) of sodium tert-butoxide. The mixture was heated at reflux for 16 h, diluted with ethyl acetate, filtered, washed successively with saturated aqueous sodium bicarbonate and brine, dried (MgSO4) and concentrated in vacuo. The residue was purified by column chromatography over silica gel eluted with ethyl acetate-hexanes 1:3, to afford 24 mg (36%) of the title compound as a yellow oil.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 16 h
  3. filtrationfiltered
  4. washwashed successively with saturated aqueous sodium bicarbonate and brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography over silica gel
  8. washeluted with ethyl acetate-hexanes 1:3

Quellen und Nachweise

ORD-Eintrag
ord-c2d76d0e81494c2181d7679145ab6bc4
Quelldatensatz
uspto-grants-2007_01
Patentnummer
US07169798B2

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