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

HRID 522200
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HRID 522200 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+].[I:29]I.S([O-])([O-])(=O)=S.[Na+].[Na+]>O1CCCC1.C(OCC)(=O)C.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:29])=[CH:10][C:3]=12
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참가 물질

8

반응물 4

HCID 807IodineHCID 24477Sodium ThiosulfateHCID 2724682Lithium diisopropylamideHCID 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 3

HCID 962Water
용매
HCID 8028Tetrahydrofuran용매2회
HCID 8857Ethyl Acetate용매

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온도
-78 °C

실험 절차

To a solution of Example 5A (25 g, 71.2 mmol) in tetrahydrofuran (600 ml) at −78° C. was slowly added lithium diisopropylamide (2M in tetrahydrofuran, 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 mixture was stirred for 3 hours. Saturated aqueous sodium thiosulfate, water and ethyl acetate were added and the aqueous layer was extracted with ethyl acetate. The combined organics were dried over sodium sulfate, filtered and concentrated to provide the title compound. MS (CI) m/z 477 (M+H)+.

후처리

  1. customat −78° C.
  2. stirringthe mixture was stirred for 3 hours
  3. extractionthe aqueous layer 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-90cca419899b40068dd5fe4ea2482ee1
출처 데이터셋
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09328112B2

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