N-{4-chloro-2-fluoro-5-[(5-nitropyridin-2-yl)oxy]phenyl}-2,2,2-trifluoroacetamide → N-{5-[(5-aminopyridin-2-yl)oxy]-4-chloro-2-fluorophenyl}-2,2,2-trifluoroacetamide

HRID 1800540ノート

反応式

HRID 1800540 の反応式
[Cl:1][C:2]1[C:7]([O:8][C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][N:10]=2)=[CH:6][C:5]([NH:18][C:19](=[O:24])[C:20]([F:23])([F:22])[F:21])=[C:4]([F:25])[CH:3]=1>C(O)(=O)C>[NH2:15][C:12]1[CH:13]=[CH:14][C:9]([O:8][C:7]2[C:2]([Cl:1])=[CH:3][C:4]([F:25])=[C:5]([NH:18][C:19](=[O:24])[C:20]([F:23])([F:21])[F:22])[CH:6]=2)=[N:10][CH:11]=1

参加物

3

反応物 1

HCID 86646017N-{4-chloro-2-fluoro-5-[(5-nitropyridin-2-yl)oxy]phenyl}-2,2,2-trifluoroacetamide

生成物 1

HCID 86646018N-{5-[(5-aminopyridin-2-yl)oxy]-4-chloro-2-fluorophenyl}-2,2,2-trifluoroacetamide収率 65%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
60 °C

実験手順

A mixture of N-{4-chloro-2-fluoro-5-[(5-nitropyridin-2-yl)oxy]phenyl}-2,2,2-trifluoroacetamide (600 mg, 1.58 mmol), reduced iron (452 mg, 8.09 mmol) and acetic acid (10 mL) was stirred at 60° C. for 1.5 hr. The reaction mixture was filtered through celite, and the filtrate was concentrated under reduced pressure. The residue was dissolved in ethyl acetate (20 mL), washed with saturated aqueous sodium hydrogen carbonate solution (10 mL) and saturated brine (10 mL), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=80/20→34/66) to give the title compound (357 mg, 65%) as a white powder.

後処理

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in ethyl acetate (20 mL)
  4. washwashed with saturated aqueous sodium hydrogen carbonate solution (10 mL) and saturated brine (10 mL)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=80/20→34/66)

出典と根拠

ORDレコード
ord-95518fe692f844e19228643dcfd4bc27
出典データセット
uspto-grants-2013_01
特許番号
US08344135B2

反応ノート

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