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Pyridine → 7-(Benzyloxy)-5-[4-(methylsulfonyl)phenoxy]-1H-indole-2-carbonitrile

HRID 1188877
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1188877
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([O:21][C:22]2[CH:27]=[CH:26][C:25]([S:28]([CH3:31])(=[O:30])=[O:29])=[CH:24][CH:23]=2)[CH:12]=[C:13]2[C:17]=1[NH:16][C:15]([C:18]([NH2:20])=O)=[CH:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.CN(C)C=O.C(Cl)(=O)C(Cl)=O>O>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([O:21][C:22]2[CH:23]=[CH:24][C:25]([S:28]([CH3:31])(=[O:30])=[O:29])=[CH:26][CH:27]=2)[CH:12]=[C:13]2[C:17]=1[NH:16][C:15]([C:18]#[N:20])=[CH:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 1049Pyridine2×HCID 6228DimethylformamideHCID 65578Oxalyl chloride2×HCID 668976427-(Benzyloxy)-5-[4-(methylsulfonyl)phenoxy]-1H-indole-2-carboxamide

Produkt 1

HCID 668975217-(Benzyloxy)-5-[4-(methylsulfonyl)phenoxy]-1H-indole-2-carbonitrileAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 962WaterLösungsmittel

Versuchsvorschrift

To a mixture of 7-(benzyloxy)-5-[4-(methylsulfonyl)phenoxy]-1H-indole-2-carboxamide (840 mg), pyridine (0.23 mL) and N,N-dimethylformamide (20 mL) was added dropwise oxalyl chloride (0.25 mL) under ice-cooling, and the mixture was stirred for 2 hr. Pyridine (0.23 mL) and oxalyl chloride (0.25 mL) were successively added, and the mixture was further stirred for 30 min. Water was added to the reaction solution, and the mixture was subjected to extraction with ethyl acetate. The organic layer was washed successively with 1M hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The obtained solid was washed with a mixed solvent of diethyl ether-hexane to give the title compound (660 mg, yield 92%) as yellow crystals. The obtained yellow crystals were recrystallized from ethanol-hexane to give yellow crystals. melting point 209-210° C.

Aufarbeitung

  1. temperaturecooling
  2. stirringthe mixture was further stirred for 30 min
  3. extractionthe mixture was subjected to extraction with ethyl acetate
  4. washThe organic layer was washed successively with 1M hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution and saturated brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. washThe obtained solid was washed with a mixed solvent of diethyl ether-hexane

Quellen und Nachweise

ORD-Eintrag
ord-34cb040feda8427a8638daa28a4669b2
Quelldatensatz
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08673942B2

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