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

HRID 1515599Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1515599
[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

Komponenten

5

Edukt 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

Produkt 1

HCID 497590181H-Pyrrolo[2,3-B]pyridine, 5-bromo-1-[(1,1-dimethylethyl)dimethylsilyl]-Ausbeute 97,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-bfcab5cb4c2f4dac8e0754b57374b24e
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08222416B2

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