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Dimethylformamide → 1-[Bis(4-fluorophenyl)methyl]-2-formyl-4,6-dimethyl-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile

HRID 730434
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 730434
C(NC(C)C)(C)C.C([Li])CCC.CCCCCC.[F:19][C:20]1[CH:25]=[CH:24][C:23]([CH:26]([C:40]2[CH:45]=[CH:44][C:43]([F:46])=[CH:42][CH:41]=2)[N:27]2[C:31]3=[N:32][C:33]([CH3:37])=[CH:34][C:35]([CH3:36])=[C:30]3[C:29]([C:38]#[N:39])=[CH:28]2)=[CH:22][CH:21]=1.CN(C)[CH:49]=[O:50]>O1CCCC1.O>[F:46][C:43]1[CH:42]=[CH:41][C:40]([CH:26]([C:23]2[CH:24]=[CH:25][C:20]([F:19])=[CH:21][CH:22]=2)[N:27]2[C:31]3=[N:32][C:33]([CH3:37])=[CH:34][C:35]([CH3:36])=[C:30]3[C:29]([C:38]#[N:39])=[C:28]2[CH:49]=[O:50])=[CH:45][CH:44]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 5

HCID 6228DimethylformamideHCID 7912DiisopropylamineHCID 8058HexaneHCID 690625951-[Bis(4-fluorophenyl)methyl]-4,6-dimethyl-1H-pyrrolo[2,3-b]pyridine-3-carbonitrileHCID 178418339Butyllithium

Produkt 1

HCID 86760956
1-[Bis(4-fluorophenyl)methyl]-2-formyl-4,6-dimethyl-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a solution of diisopropylamine (5.27 ml, 40.2 mmol) in tetrahydrofuran (50 ml) was added a 1.6 N solution of butyllithium in hexane (25.1 ml, 40.2 mmol) at −78° C., which was stirred at −78° C. for 15 minutes. To the resultant solution was added dropwise 1-[bis(4-fluorophenyl)methyl]-4,6-dimethyl-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile (11.6 g, 31.1 mmol) at −78° C., and the mixture was stirred at −78° C. for 30 minutes. Dimethylformamide (6.23 ml, 80.4 mmol) was added thereto, and the mixture was stirred at room temperature for 1.5 hours, poured into iced water and extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to give the objective product as a solid material.

Aufarbeitung

  1. stirringthe mixture was stirred at −78° C. for 30 minutes
  2. stirringthe mixture was stirred at room temperature for 1.5 hours
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-a6318c43e97a4c3a9d59ac3ab2e91a55
Quelldatensatz
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07582651B2

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