2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 1H-Pyrrolo[2,3-B]pyridine, 5-bromo-1-[(1,1-dimethylethyl)dimethylsilyl]-

HRID 1515599노트

반응식

HRID 1515599 반응식
[Br:1][C:2]1[CH:3]=[C:4]2[CH2:10][CH2:9][N:8]([Si:11]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12])[C:5]2=[N:6][CH:7]=1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>ClCCl.C(=O)(O)[O-].[Na+]>[Br:1][C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][N:8]([Si:11]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:12])[CH3:13])[C:5]2=[N:6][CH:7]=1

참가 물질

5

반응물 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 587309295-Bromo-1-(tert-butyl-dimethyl-silanyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine

생성물 1

HCID 497590181H-Pyrrolo[2,3-B]pyridine, 5-bromo-1-[(1,1-dimethylethyl)dimethylsilyl]-수율 97.6%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 516892Sodium Bicarbonate용매

실험 절차

To a stirred solution of 5-bromo-1-(tert-butyl-dimethyl-silanyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine (17.0 g, 54.3 mmol) in dichloromethane (700 mL) was added 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (12.3 g, 54.3 mmol) in one portion. After 1 h, the resulting black mixture was diluted with a saturated aqueous sodium bicarbonate solution and stirred vigorously for 30 min. The solids were filtered off and the filtrate was separated. The aqueous layer was extracted with ethyl acetate. The combined organic solutions were dried over anhydrous sodium sulfate, concentrated in vacuo to afford 5-bromo-1-(tert-butyl-dimethyl-silanyl)-1H-pyrrolo[2,3-b]pyridine (16.5 g, 97%) which was used in the next step without further purification: 1H NMR (400 MHz, CDCl3) δ ppm 0.64 (s, 6H), 0.94 (s, 9H), 6.49 (d, J=3.4 Hz, 1H), 7.27 (d, J=3.4 Hz, 1H), 8.00 (d, J=2.3 Hz, 1H), 8.31 (d, J=2.3 Hz, 1H).

후처리

  1. filtrationThe solids were filtered off
  2. customthe filtrate was separated
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. dry with materialThe combined organic solutions were dried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-bfcab5cb4c2f4dac8e0754b57374b24e
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08222416B2

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