Acetic Acid → 6-fluoro-5-methyl-1H-indole

HRID 1674590ノート

反応式

HRID 1674590 の反応式
C(OC(=O)[CH:10]([C:22]#[N:23])[C:11]1[CH:16]=[C:15]([CH3:17])[C:14]([F:18])=[CH:13][C:12]=1[N+]([O-])=O)C1C=CC=CC=1.C(O)(=O)C.O.[H][H]>C(O)C.[C].[Pd]>[F:18][C:14]1[CH:13]=[C:12]2[C:11]([CH:10]=[CH:22][NH:23]2)=[CH:16][C:15]=1[CH3:17]

参加物

7

反応物 4

HCID 176Acetic AcidHCID 962Water2 回HCID 58437495Benzyl 2-cyano-2-(4-fluoro-5-methyl-2-nitrophenyl)acetateHCID 178418361HCID 178418361、化合物

生成物 1

HCID 27746116-fluoro-5-methyl-1H-indole収率 76.6%

試薬・触媒・溶媒 2

HCID 178418390HCID 178418390、化合物触媒HCID 702Ethanol溶媒

実験手順

To a solution of cyano-(4-fluoro-5-methyl-2-nitrophenyl)acetic acid benzyl ester (1.54 g), acetic acid (7 mL) and water (7 mL) in ethanol (15 mL) was added 10% palladium-carbon (0.154 g) under an argon atmosphere. This reaction mixture was stirred at room temperature for 60 hours under a hydrogen atmosphere. After water was added to this reaction mixture, hydrogen was exchanged by argon. The insoluble material was removed by filtration, and this filtrate was extracted with diethyl ether. This organic layer was washed with brine, and dried over anhydrous magnesium sulfate, and filtered. The solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: ethyl acetate/n-hexane=75/25) to give the title compound (0.536 g).

後処理

  1. customThe insoluble material was removed by filtration
  2. extractionthis filtrate was extracted with diethyl ether
  3. washThis organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customThe solvent was removed under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel (eluent: ethyl acetate/n-hexane=75/25)

出典と根拠

ORDレコード
ord-d972bf12108e403aa7207bcad86c34ea
出典データセット
uspto-grants-2011_08
特許番号
US08003647B2

反応ノート

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