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

HRID 561208ノート

反応式

HRID 561208 の反応式
[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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 7964Chlorobenzene溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-091711a9d51d4572a203552b8c604b9d
出典データセット
uspto-grants-2011_11
特許番号
US08063224B2

反応ノート

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