Calcium Chloride → 3-Fluoro-4-{[3-(1-methyl-1H-pyrazol-5-yl)biphenyl-4-yl]oxy}aniline

HRID 1619645ノート

反応式

HRID 1619645 の反応式
[F:1][C:2]1[CH:26]=[C:25]([N+:27]([O-])=O)[CH:24]=[CH:23][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:7][C:6]=1[C:17]1[N:21]([CH3:22])[N:20]=[CH:19][CH:18]=1.[Cl-].[Cl-].[Ca+2]>C(O)C.O.[Fe]>[F:1][C:2]1[CH:26]=[C:25]([CH:24]=[CH:23][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:7][C:6]=1[C:17]1[N:21]([CH3:22])[N:20]=[CH:19][CH:18]=1)[NH2:27]

参加物

6

反応物 2

HCID 5284359Calcium ChlorideHCID 580422745-[4-(2-Fluoro-4-nitrophenoxy)biphenyl-3-yl]-1-methyl-1H-pyrazole

生成物 1

HCID 580423493-Fluoro-4-{[3-(1-methyl-1H-pyrazol-5-yl)biphenyl-4-yl]oxy}aniline収率 84%

試薬・触媒・溶媒 3

HCID 23925Iron触媒HCID 702Ethanol溶媒HCID 962Water溶媒

実験手順

5-[4-(2-Fluoro-4-nitrophenoxy)biphenyl-3-yl]-1-methyl-1H-pyrazole (Preparation 29, 870 mg, 2.33 mmol) was dissolved in ethanol (8 mL) and water (2 mL). Iron powder (624 mg, 11.17 mmol) and CaCl2 (248 mg, 2.33 mmol) were then added and the reaction mixture was refluxed for 3 hours. After filtration through Celite™, the filtrate was concentrated in vacuo. The residue was partitioned between dichloromethane and water. The organic layer was separated, washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (100-200 mesh silica gel, 15% ethyl acetate in hexane) to afford the title compound (700 mg, 84%).

後処理

  1. temperaturethe reaction mixture was refluxed for 3 hours
  2. filtrationAfter filtration through Celite™
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe residue was partitioned between dichloromethane and water
  5. customThe organic layer was separated
  6. washwashed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified by silica gel column chromatography (100-200 mesh silica gel, 15% ethyl acetate in hexane)

出典と根拠

ORDレコード
ord-1e11bcb1f2274071be1bedf4ec818b52
出典データセット
uspto-grants-2014_07
特許番号
US08772293B2

反応ノート

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