alpha-Chloro-m-nitrotoluene → 3-(3,4-Dimethoxy-phenyl)-1-(3-nitro-benzyl)-1H-pyrrolo[2,3-b]pyridine

HRID 1820890Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1820890
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[CH:17][CH:18]=3)[NH:13][CH:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[H-].[Na+].[N+:22]([C:25]1[CH:26]=[C:27]([CH:30]=[CH:31][CH:32]=1)[CH2:28]Cl)([O-:24])=[O:23]>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[CH:17][CH:18]=3)[N:13]([CH2:28][C:27]3[CH:30]=[CH:31][CH:32]=[C:25]([N+:22]([O-:24])=[O:23])[CH:26]=3)[CH:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Komponenten

5

Edukt 3

HCID 12078alpha-Chloro-m-nitrotolueneHCID 24758Sodium hydrideHCID 116732853-(3,4-dimethoxy-phenyl)-1H-pyrrolo[2,3-b]pyridine

Produkt 1

HCID 578917543-(3,4-Dimethoxy-phenyl)-1-(3-nitro-benzyl)-1H-pyrrolo[2,3-b]pyridineAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

3-(3,4-Dimethoxy-phenyl)-1H-pyrrolo[2,3-b]pyridine 1 (35 mg, 0.14 mmole) was dissolved in 15 mL of DMF and sodium hydride (60% dispersion in mineral oil, 10 mg, 0.25 mmol) was added in small portion to the reaction mixture. After stirring for 30 minutes, m-nitro-benzyl chloride (30 mg, 0.14 mmole) was added to the reaction mixture and was stirred for 2 hours. The reaction mixture was poured into 50 mL of ice water and was extracted with ethyl acetate. The organic layer was washed with saturated sodium bicarbonate followed by saturated potassium bisulfate and then brine. The resulting solution was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography (30% ethyl acetate in hexanes) to yield 42 mg (71%) of the titled compound as a white solid. MS(ESI) [M+H+]+=390.1.

Aufarbeitung

  1. stirringwas stirred for 2 hours
  2. extractionwas extracted with ethyl acetate
  3. washThe organic layer was washed with saturated sodium bicarbonate
  4. dry with materialThe resulting solution was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel chromatography (30% ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-4ff113348dd74e3cac51b3bad10beb82
Quelldatensatz
uspto-grants-2009_10
Patentnummer
US07605168B2

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