Iodine → 3-[4-(2-Bromo-5-fluorophenoxy)piperidin-1-yl]isoxazole-5-carboxamide

HRID 561208노트

반응식

HRID 561208 반응식
[Br:1][C:2]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:3]=1[O:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH2:15][CH:14]([C:16]([NH2:18])=[O:17])[O:13][N:12]=2)[CH2:7][CH2:6]1.C([O-])(=O)C.[Na+].II.[O-]S([O-])(=S)=O.[Na+].[Na+]>ClC1C=CC=CC=1.CCOC(C)=O.O>[Br:1][C:2]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:3]=1[O:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:15]=[C:14]([C:16]([NH2:18])=[O:17])[O:13][N:12]=2)[CH2:7][CH2:6]1

참가 물질

8

반응물 4

HCID 807IodineHCID 24477Sodium ThiosulfateHCID 517045Sodium AcetateHCID 666968003-[4-(2-Bromo-5-fluorophenoxy)piperidin-1-yl]-4,5-dihydroisoxazole-5-carboxamide

생성물 1

HCID 533885293-[4-(2-Bromo-5-fluorophenoxy)piperidin-1-yl]isoxazole-5-carboxamide

시약·촉매·용매 3

HCID 962Water용매HCID 7964Chlorobenzene용매HCID 8857Ethyl Acetate용매

실험 절차

To a stirred suspension of 3-[4-(2-bromo-5-fluorophenoxy)piperidin-1-yl]-4,5-dihydroisoxazole-5-carboxamide (2.3 g, 5.96 mmol) and sodium acetate (1.3 g, 15.85 mmol) in chlorobenzene (15 mL) was added iodine (2 g, 7.88 mmol). The mixture was heated at reflux temperature for 3 h. After cooling, a solution of Na2S2O3, water and EtOAc were added. The mixture was stirred for 5 min and filtered through celite to remove the insoluble material. The organic layer was then separated, washed with brine, dried (Na2SO4) and concentrated. The residue was triturated with Et2O to give the title compound as light brown powder.

후처리

  1. temperatureThe mixture was heated
  2. temperatureat reflux temperature for 3 h
  3. temperatureAfter cooling
  4. filtrationfiltered through celite
  5. customto remove the insoluble material
  6. customThe organic layer was then separated
  7. washwashed with brine
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated
  10. customThe residue was triturated with Et2O

출처 및 근거

ORD 기록
ord-091711a9d51d4572a203552b8c604b9d
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08063224B2

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