1,2-Dimethoxyethane → 3,5-Dimethyl-4-[2-(methyloxy)-5-nitrophenyl]isoxazole

HRID 1042997

반응식

HRID 1042997 반응식
I[C:2]1[CH:3]=[C:4]([N+:10]([O-:12])=[O:11])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[CH3:13][C:14]1[C:18](B(O)O)=[C:17]([CH3:22])[O:16][N:15]=1.C(=O)([O-])[O-].[Cs+].[Cs+].COCCOC>C(OCC)(=O)C.O>[CH3:13][C:14]1[C:18]([C:2]2[CH:3]=[C:4]([N+:10]([O-:12])=[O:11])[CH:5]=[CH:6][C:7]=2[O:8][CH3:9])=[C:17]([CH3:22])[O:16][N:15]=1

참가 물질

7

반응물 4

HCID 80711,2-DimethoxyethaneHCID 10796Cesium carbonateHCID 948062-Iodo-1-methoxy-4-nitrobenzeneHCID 27343463,5-Dimethylisoxazole-4-boronic acid

생성물 1

HCID 574655703,5-Dimethyl-4-[2-(methyloxy)-5-nitrophenyl]isoxazole수율 83.3%

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매

반응 조건

온도
90 °C

실험 절차

3-Iodo-4-(methoxy) nitrobenzene (65 g, 233 mmol, Matrix Scientific), (3,5-dimethyl-4-isoxazolyl)boronic acid (36.1 g, 256 mmol) and cesium carbonate (152 g, 466 mmol) were combined with DME (80 ml) and water (40 ml) and the mixture was degassed with nitrogen for 10 min, then PEPPSI™ catalyst (3.96 g, 5.82 mmol) was added and the mixture heated at 90° C. for 4 h, then cooled and diluted with ethyl acetate (800 ml). The resulting suspension was filtered through Celite and the filtrate washed with water (2×500 ml). The solvent was dried (sodium sulphate), filtered and evaporated to give a brown solid which was triturated with ether (30 ml). The solid product was washed with ether (100 ml) to give 3,5-dimethyl-4-[2-(methyloxy)-5-nitrophenyl]isoxazole as beige solid (48.2 g).

후처리

  1. customthe mixture was degassed with nitrogen for 10 min
  2. temperaturecooled
  3. filtrationThe resulting suspension was filtered through Celite
  4. washthe filtrate washed with water (2×500 ml)
  5. dry with materialThe solvent was dried (sodium sulphate)
  6. filtrationfiltered
  7. customevaporated
  8. customto give a brown solid which
  9. customwas triturated with ether (30 ml)
  10. washThe solid product was washed with ether (100 ml)

출처 및 근거

ORD 기록
ord-f92accf7167c4fe5bdab9d8575060449
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08557984B2

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