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

HRID 1375631ノート

反応式

HRID 1375631 の反応式
[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

参加物

8

反応物 4

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

生成物 1

HCID 9949334[4-(5-Methyl-3-phenyl-isoxazol-4-yl)-pyrimidin-2-yl]-phenyl-amine収率 36.5%

試薬・触媒・溶媒 3

HCID 9832798Tris(dibenzylideneacetone) dipalladium触媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-c2d76d0e81494c2181d7679145ab6bc4
出典データセット
uspto-grants-2007_01
特許番号
US07169798B2

反応ノート

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