Water → 6-Nitro-2-phenyl-1H-indole

HRID 1886956ノート

反応式

HRID 1886956 の反応式
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:16]#[C:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:8]([NH:10]C(=O)CCC)[CH:9]=1)([O-:3])=[O:2].CC(C)([O-])C.[K+].O>CN1CCCC1=O>[N+:1]([C:4]1[CH:9]=[C:8]2[C:7]([CH:16]=[C:17]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[NH:10]2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

参加物

5

反応物 3

HCID 962WaterHCID 11358741N-(5-Nitro-2-(phenylethynyl)phenyl)butyramideHCID 23665647Potassium tert-butoxide

生成物 1

HCID 207598016-Nitro-2-phenyl-1H-indole収率 39.1%

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
70 °C

実験手順

To a solution of N-(5-nitro-2-(phenylethynyl)phenyl)butyramide (580 mg, 1.88 mmol) in 1-Methyl-2-pyrrolidinone (20 mL) under nitrogen was added potassium tert-butoxide (243 mg, 2.16 mmol). The resulting solution was heated at 70° C. for 6 h, and then left at room temperature for 16 h. Water was added and the aqueous layer was extracted several times with ethyl acetate. The combined organic layers were washed 10 times with water, 3 times with brine, dried over anhydrous MgSO4 and evaporated. The resulting material was purified by column chromatography eluting with ethyl acetate/hexanes 15:85 v/v to afford 175 mg (39%) of the title compound.

後処理

  1. extractionthe aqueous layer was extracted several times with ethyl acetate
  2. washThe combined organic layers were washed 10 times with water, 3 times with brine
  3. dry with materialdried over anhydrous MgSO4
  4. customevaporated
  5. customThe resulting material was purified by column chromatography
  6. washeluting with ethyl acetate/hexanes 15:85 v/v

出典と根拠

ORDレコード
ord-00bddab197664497b06e24ad3ba84ae9
出典データセット
uspto-grants-2013_08
特許番号
US08501713B2

反応ノート

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