Water → 6-Nitro-2-phenyl-1H-indole

HRID 1896788노트

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HRID 1896788 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 207598016-Nitro-2-phenyl-1H-indole수율 39.1%

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

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온도
70 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-04af9c92c9eb466a99d6543159a81978
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08518980B2

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