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Tert-butyl {3-fluoro-4-[(5-nitropyridin-2-yl)oxy]phenyl}carbamate → Tert-butyl {4-[(5-aminopyridin-2-yl)oxy]-3-fluorophenyl}carbamate

HRID 2095772
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HRID 2095772 반응식
[F:1][C:2]1[CH:3]=[C:4]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][N:10]=1>CO.[Pd]>[NH2:15][C:12]1[CH:13]=[CH:14][C:9]([O:8][C:7]2[CH:6]=[CH:5][C:4]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])=[CH:3][C:2]=2[F:1])=[N:10][CH:11]=1
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참가 물질

4

반응물 1

HCID 58158596Tert-butyl {3-fluoro-4-[(5-nitropyridin-2-yl)oxy]phenyl}carbamate

생성물 1

HCID 58158488Tert-butyl {4-[(5-aminopyridin-2-yl)oxy]-3-fluorophenyl}carbamate수율 90%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

실험 절차

To a suspension of tert-butyl {3-fluoro-4-[(5-nitropyridin-2-yl)oxy]phenyl}carbamate (15 g, 42.9 mmol) in methanol (300 mL) was added 5 wt % palladium/carbon (3.0 g), and the mixture was stirred at room temperature for 8 hr under a hydrogen atmosphere. After nitrogen substitution, insoluble material was collected by filtration and washed with methanol. The solvent of the filtrate was evaporated under reduced pressure, water was added to the residue, and the mixture was extracted with ethyl acetate/tetrahydrofuran. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and filtered. The solvent was evaporated under reduced pressure to give the title compound (12.3 g, 90%).

후처리

  1. filtrationAfter nitrogen substitution, insoluble material was collected by filtration
  2. washwashed with methanol
  3. customThe solvent of the filtrate was evaporated under reduced pressure, water
  4. additionwas added to the residue
  5. extractionthe mixture was extracted with ethyl acetate/tetrahydrofuran
  6. washThe organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customThe solvent was evaporated under reduced pressure

출처 및 근거

ORD 기록
ord-dd13b4f1c11746f785b37c6129310d92
출처 데이터셋
uspto-grants-2013_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08445509B2

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