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Iodine → 4-Bromo-2-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridine

HRID 871100
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HRID 871100 반응식
[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([S:11]([C:14]3[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=3)(=[O:13])=[O:12])[CH:9]=[CH:10][C:3]=12.C([N-]C(C)C)(C)C.[Li+].CCCCCCC.O1CCCC1.C(C1C=CC=CC=1)C.[I:49]I.S([O-])([O-])(=O)=S.[Na+].[Na+]>O1CCCC1.O>[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([S:11]([C:14]3[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=3)(=[O:13])=[O:12])[C:9]([I:49])=[CH:10][C:3]=12
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참가 물질

8

반응물 5

HCID 807IodineHCID 24477Sodium ThiosulfateHCID 2724682Lithium diisopropylamideHCID 22742125Tetrahydrofuran heptane ethylbenzolHCID 378186494-Bromo-1-(4-methylbenzene-1-sulfonyl)-1H-pyrrolo[2,3-b]pyridine

생성물 1

HCID 378186504-Bromo-2-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridine

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

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온도
-78 °C

실험 절차

To a solution of Example 36A (25 g, 71.2 mmol) in tetrahydrofuran (600 mL) at −78° C. was added slowly 2M lithium diisopropylamide in heptane/tetrahydrofuran/ethyl benzene (39.1 mL, 78 mmol) and the mixture was stirred at −78° C. for 1 hour. A solution of iodine (19.87 g, 78 mmol) in tetrahydrofuran (100 mL) was added slowly and the reaction was allowed to warm gradually to room temperature. The reaction mixture was stirred at room temperature for 3 hours. Saturated aqueous sodium thiosulfate and water were added and the mixture was extracted with ethyl acetate. The combined organics were dried over sodium sulfate, filtered, and concentrated to give the title compound.

후처리

  1. temperatureto warm gradually to room temperature
  2. stirringThe reaction mixture was stirred at room temperature for 3 hours
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe combined organics were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-5499a85e81b44196befc737e034ff084
출처 데이터셋
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08969375B2

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