Acetone → 6-(2-Chlorophenylamino)-7-fluoro-3-methyl-benzo[c]-isoxazole-5-carboxylic acid methyl ester

HRID 494723노트

반응식

HRID 494723 반응식
[N-:1]=[N+]=[N-].[Na+].[CH3:5][O:6][C:7](=[O:27])[C:8]1[CH:13]=[C:12]([C:14](=[O:16])[CH3:15])[C:11](F)=[C:10]([F:18])[C:9]=1[NH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[Cl:26].CC(C)=O>CCOC(C)=O.O>[CH3:5][O:6][C:7]([C:8]1[C:9]([NH:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[Cl:26])=[C:10]([F:18])[C:11]2=[N:1][O:16][C:14]([CH3:15])=[C:12]2[CH:13]=1)=[O:27]

참가 물질

6

반응물 3

HCID 180AcetoneHCID 33557Sodium AzideHCID 865967735-Acetyl-2-(2-chlorophenylamino)-3,4-difluorobenzoic acid methyl ester

생성물 1

HCID 688605096-(2-Chlorophenylamino)-7-fluoro-3-methyl-benzo[c]-isoxazole-5-carboxylic acid methyl ester수율 77%

시약·촉매·용매 2

HCID 962Water용매2회HCID 8857Ethyl Acetate용매

실험 절차

Sodium azide (128 mg, 1.95 mmol) was added to a mixture of 5-acetyl-2-(2-chlorophenylamino)-3,4-difluorobenzoic acid methyl ester (6) (601 mg, 1.59 mmol) in 3:1 acetone:water (16 ml) and heated to reflux. After 16 hours, the reaction mixture was cooled to room temperature, and diluted with EtOAc and water. The organic layer was washed with water, dried (MgSO4) and concentrated. The resulting residue was diluted with water (8 mL) and heated to reflux. After 5 hours, the mixture was cooled to room temperature and diluted with EtOAc. The organic layer was washed with water, dried (MgSO4) and concentrated. Purification by flash column chromatography using the Biotage system (20% EtOAc in hexanes) provided the desired product (55) (410 mg, 77%).

후처리

  1. washThe organic layer was washed with water
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. additionThe resulting residue was diluted with water (8 mL)
  5. temperatureheated to reflux
  6. waitAfter 5 hours
  7. temperaturethe mixture was cooled to room temperature
  8. additiondiluted with EtOAc
  9. washThe organic layer was washed with water
  10. dry with materialdried (MgSO4)
  11. concentrationconcentrated
  12. customPurification by flash column chromatography

출처 및 근거

ORD 기록
ord-c042b036c0af490faa2d4af898a63a7f
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07538120B2

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