Water → 9-oxo-9H-pyrrolo[1,2-a]indole-5-carboxylic acid methyl ester

HRID 1925561노트

반응식

HRID 1925561 반응식
B(Br)(Br)Br.CO[C:7](=[O:23])[C:8]1[CH:17]=[CH:16][CH:15]=[C:10]([C:11]([O:13][CH3:14])=[O:12])[C:9]=1[N:18]1[CH:22]=[CH:21][CH:20]=[CH:19]1.O>ClCCl>[CH3:14][O:13][C:11]([C:10]1[CH:15]=[CH:16][CH:17]=[C:8]2[C:9]=1[N:18]1[CH:19]=[CH:20][CH:21]=[C:22]1[C:7]2=[O:23])=[O:12]

참가 물질

5

반응물 3

HCID 962WaterHCID 25134Boron tribromideHCID 13113670Dimethyl 2-(1H-pyrrol-1-yl)benzene-1,3-dicarboxylate

생성물 1

HCID 672994649-oxo-9H-pyrrolo[1,2-a]indole-5-carboxylic acid methyl ester수율 53.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

In a 50 ml round-bottomed flask, 3 ml of a 1M solution of boron tribromide in dichloromethane are added, at ambient temperature, to a mixture of 260 mg of 2-pyrrol-1-ylisophthalic acid dimethyl ester (which can be prepared according to Helvetica Chim. Acta 1983, 66(7), 2135) dissolved in 4 ml of dichloromethane. The reaction medium is stirred at ambient temperature for 2 hours and then 5 ml of water are added. After separation by settling out, the aqueous phase is re-extracted with twice 15 ml of dichloromethane. The combined organic phases are washed with twice 20 ml of water, dried over magnesium sulphate, and evaporated to dryness under vacuum. The residue is chromatographed on silica gel (15-40 μm), elution being carried out with a mixture of dichloromethane and cyclohexane (50/50 v/v). 122 mg of 9-oxo-9H-pyrrolo[1,2-a]indole-5-carboxylic acid methyl ester are obtained in the form of a yellowish solid, the characteristics of which are identical to those of the product obtained by method 1.

후처리

  1. customAfter separation
  2. extractionthe aqueous phase is re-extracted with twice 15 ml of dichloromethane
  3. washThe combined organic phases are washed with twice 20 ml of water
  4. dry with materialdried over magnesium sulphate
  5. customevaporated to dryness under vacuum
  6. customThe residue is chromatographed on silica gel (15-40 μm), elution
  7. additionbeing carried out with a mixture of dichloromethane and cyclohexane (50/50 v/v)

출처 및 근거

ORD 기록
ord-1f071fe7d74c42359df1c4c7e35e5759
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08178687B2

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