Ethanol → 2-(Benzyloxy)-3-fluoro-4-{[6-(methylsulfonyl)pyridin-3-yl]oxy}aniline

HRID 1188955ノート

反応式

HRID 1188955 の反応式
[CH2:1]([O:8][C:9]1[C:10]([F:29])=[C:11]([CH:23]=[CH:24][C:25]=1[N+:26]([O-])=O)[O:12][C:13]1[CH:14]=[CH:15][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[N:17][CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[Ca+2].[Cl-].C(O)C>[Fe].O>[CH2:1]([O:8][C:9]1[C:10]([F:29])=[C:11]([O:12][C:13]2[CH:18]=[N:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][CH:14]=2)[CH:23]=[CH:24][C:25]=1[NH2:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

6

反応物 3

HCID 702EthanolHCID 5284359Calcium ChlorideHCID 582371085-[3-(Benzyloxy)-2-fluoro-4-nitrophenoxy]-2-(methylsulfonyl)pyridine

生成物 1

HCID 582369482-(Benzyloxy)-3-fluoro-4-{[6-(methylsulfonyl)pyridin-3-yl]oxy}aniline収率 70.5%

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 962Water溶媒

実験手順

A mixture of 5-[3-(benzyloxy)-2-fluoro-4-nitrophenoxy]-2-(methylsulfonyl)pyridine (8.4 g), iron (powder, 5.5 g), calcium chloride (0.24 g), ethanol (200 mL) and water (40 mL) was refluxed for 4 h. The mixture was cooled to room temperature and filtered through a celite pad. The filtrate was concentrated in vacuo to remove ethanol. The residue was partitioned between ethyl acetate and brine. The organic layer was washed with brine, dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (ethyl acetate:hexane=20:80 to 40:60, volume ratio) to give the title compound (5.5 g, 70%) as a dark green oil. MS 389 (MH+).

後処理

  1. temperaturewas refluxed for 4 h
  2. filtrationfiltered through a celite pad
  3. concentrationThe filtrate was concentrated in vacuo
  4. customto remove ethanol
  5. customThe residue was partitioned between ethyl acetate and brine
  6. washThe organic layer was washed with brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified by silica gel chromatography (ethyl acetate:hexane=20:80 to 40:60, volume ratio)

出典と根拠

ORDレコード
ord-51e396482b914a9b98f332fae5dcef8c
出典データセット
uspto-grants-2014_03
特許番号
US08673942B2

反応ノート

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