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Methyl 2-(bromomethyl)-6-methylbenzoate → ethyl 2-(6-(7-methyl-1-oxoisoindolin-2-yl)-1H-indol-1-yl)acetate

HRID 453863
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HRID 453863 반응식
[NH2:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][N:8]2[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:4][CH:3]=1.Br[CH2:18][C:19]1[CH:28]=[CH:27][CH:26]=[C:25]([CH3:29])[C:20]=1[C:21](OC)=[O:22]>C1C=CC=CC=1.ClCCl>[CH3:18][C:19]1[CH:28]=[CH:27][CH:26]=[C:25]2[C:20]=1[C:21](=[O:22])[N:1]([C:2]1[CH:10]=[C:9]3[C:5]([CH:6]=[CH:7][N:8]3[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:4][CH:3]=1)[CH2:29]2
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참가 물질

5

반응물 2

HCID 10263795Methyl 2-(bromomethyl)-6-methylbenzoateHCID 16731704Ethyl 2-(6-amino-1H-indol-1-yl)acetate2회

생성물 1

HCID 59473657ethyl 2-(6-(7-methyl-1-oxoisoindolin-2-yl)-1H-indol-1-yl)acetate수율 64%

시약·촉매·용매 2

HCID 241Benzene용매HCID 6344Dichloromethane용매

실험 절차

Ethyl 2-(6-amino-1H-indol-1-yl)acetate (intermediate B) (7.66 mmol, 1 equiv.) was dissolved in benzene (30 ml), and methyl 2-(bromo-methyl)-6-methylbenzoate (8.42 mol, 1.1 equiv.) and TEA (9.19 mmol, 1.2 equiv.) were added at 25° C. and the mixture was refluxed for 12 h. The reaction mixture was reduced under reduced pressure and the residue was taken up in dichloromethane (30 ml), washed with water and sat. NaCl solution (5 ml), dried over sodium sulfate and concentrated under reduced pressure. The crude product was purified by column chromatography (10% ethyl acetate in hexane). Yield: 64%

후처리

  1. temperaturethe mixture was refluxed for 12 h
  2. washwashed with water and sat. NaCl solution (5 ml)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by column chromatography (10% ethyl acetate in hexane)

출처 및 근거

ORD 기록
ord-15f20744fb304cf4ba7654645aa3c242
출처 데이터셋
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08492559B2

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