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

HRID 2120854노트

반응식

HRID 2120854 반응식
[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

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 9832798Tris(dibenzylideneacetone) dipalladium촉매HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-083f390df6c944ada4fb5972d6ac3784
출처 데이터셋
uspto-grants-2004_02
특허 번호
US06693108B2

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