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Benzoyl Peroxide → 3-Chloro-4-hydroxy-1-phenyl-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester

HRID 642269
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HRID 642269 반응식
[CH2:1]([O:3][C:4]([C:6]1[C:7]([OH:21])=[C:8]2[CH:14]=[CH:13][N:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:9]2=[CH:10][N:11]=1)=[O:5])[CH3:2].C1C(=O)N([Cl:29])C(=O)C1.C(OOC(C1C=CC=CC=1)=O)(C1C=CC=CC=1)=O>C(Cl)(Cl)(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[C:7]([OH:21])=[C:8]2[C:14]([Cl:29])=[CH:13][N:12]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:9]2=[CH:10][N:11]=1)=[O:5])[CH3:2]
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참가 물질

5

반응물 3

HCID 7187Benzoyl PeroxideHCID 31398ChlorosuccinimideHCID 684267014-Hydroxy-1-phenyl-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester

생성물 1

HCID 684287393-Chloro-4-hydroxy-1-phenyl-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester수율 40%

시약·촉매·용매 1

HCID 5943Carbon Tetrachloride용매

실험 절차

A mixture of 4-hydroxy-1-phenyl-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester (223 mg, 0.789 mmol), NCS (117 mg, 0.869 mmol) and BzOOBz (10 mg, 0.039 mmol) in carbontetrachloride (4 mL) was refluxed for 30 min. Then the reaction was cooled and concentrated, the resulting mixture was purified by column to give the desired product (100 mg). The title compound, 1H NMR (200 MHz, CDCl3): δ (ppm)=11.8 (s, 1H), 8.44 (s, 1H), 7.6-7.4 (m, 5H), 7.35 (s, 1H), 4.53 (q, 2H, J=7.4 Hz), 1.49 (t, 3H, J=7.4 Hz).

후처리

  1. temperaturewas refluxed for 30 min
  2. temperatureThen the reaction was cooled
  3. concentrationconcentrated
  4. customthe resulting mixture was purified by column

출처 및 근거

ORD 기록
ord-97505596a6de45589efffadac3d22563
출처 데이터셋
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07696223B2

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