2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 1-(tert-Butyl-dimethyl-silanyl)-5-methyl-1H-pyrrolo[2,3-b]pyridine

HRID 1994188Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1994188
[C:1]([Si:5]([CH3:17])([CH3:16])[N:6]1[C:10]2=[N:11][CH:12]=[C:13]([CH3:15])[CH:14]=[C:9]2[CH2:8][CH2:7]1)([CH3:4])([CH3:3])[CH3:2].C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>C(Cl)Cl.C([O-])(O)=O.[Na+]>[C:1]([Si:5]([CH3:17])([CH3:16])[N:6]1[C:10]2=[N:11][CH:12]=[C:13]([CH3:15])[CH:14]=[C:9]2[CH:8]=[CH:7]1)([CH3:4])([CH3:3])[CH3:2]

Komponenten

5

Edukt 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 575977571-(tert-Butyl-dimethyl-silanyl)-5-methyl-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine

Produkt 1

HCID 575978501-(tert-Butyl-dimethyl-silanyl)-5-methyl-1H-pyrrolo[2,3-b]pyridine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

To a stirred solution of the crude azaindoline 7 (0.64 mmol) in CH2Cl2 (10 mL) was added DDQ (145 mg, 0.64 mmol) in one portion. After 20 min the resulting black mixture was diluted with saturated aqueous NaHCO3 solution and stirred vigorously for 15 min. The aqueous layer was extracted with CHCl3 (2×) and the combined organic solutions were dried (MgSO4), filtered and concentrated to afford azaindole 8 as a brown oil, which was used directly in the next step without purification.

Aufarbeitung

  1. extractionThe aqueous layer was extracted with CHCl3 (2×)
  2. dry with materialthe combined organic solutions were dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-89e7897693094c5c86e2c7fa7ce0bb28
Quelldatensatz
uspto-grants-2010_01
Patentnummer
US07652137B2

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