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Dimethylformamide → HCID 22467205, Verbindung

HRID 381335
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 381335
C([Li])CCC.Br[C:7]1[CH:15]=[C:14]2[C:10]([C:11]([CH:17]([C:33]3[CH:41]=[C:40]([O:42][CH3:43])[C:36]4[O:37][CH2:38][O:39][C:35]=4[CH:34]=3)[C:18]([NH:20][S:21]([C:24]3[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][C:25]=3[O:31][CH3:32])(=[O:23])=[O:22])=[O:19])=[CH:12][N:13]2[CH3:16])=[CH:9][CH:8]=1.CN(C)[CH:46]=[O:47]>O1CCCC1>[CH:46]([C:7]1[CH:15]=[C:14]2[C:10]([C:11]([CH:17]([C:33]3[CH:41]=[C:40]([O:42][CH3:43])[C:36]4[O:37][CH2:38][O:39][C:35]=4[CH:34]=3)[C:18]([NH:20][S:21]([C:24]3[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][C:25]=3[O:31][CH3:32])(=[O:23])=[O:22])=[O:19])=[CH:12][N:13]2[CH3:16])=[CH:9][CH:8]=1)=[O:47]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 6228DimethylformamideHCID 22467218HCID 22467218, VerbindungHCID 178418339Butyllithium

Produkt 1

HCID 22467205HCID 22467205, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

n-Butyllithium (0.8 ml of 2.5 M solution in hexane) was added to a stirred solution of 6-bromo-3-{1-(7-methoxy-1,3-benzodioxol-5-yl)-2-[(2-methoxy-4-methylphenyl)-sulfonamido]-2-oxoethyl}-1-methyl-1H-indole (from Example 92, 400 mg, 0.67 mmol) in anhydrous tetrahydrofuran at −75° C. under a nitrogen atmosphere. After 30 minutes dimethylformamide (0.15 ml) was added to the orange solution, and after a further 30 minutes the mixture was allowed to warm to 0° C. before quenching with excess 1 N hydrochloric acid. Ethyl acetate was added and the organic layer was separated and washed with water. The organic layer was dried (magnesium sulphate), and the solvents removed in vacuo. The residue was flash chromatographed using 1% methanol in dichloromethane as eluant, and the product was crystallised from dichloromethane and diethyl ether mixture to give the title compound (187 mg).

Aufarbeitung

  1. custombefore quenching with excess 1 N hydrochloric acid
  2. additionEthyl acetate was added
  3. customthe organic layer was separated
  4. washwashed with water
  5. dry with materialThe organic layer was dried (magnesium sulphate)
  6. customthe solvents removed in vacuo
  7. customchromatographed
  8. customthe product was crystallised from dichloromethane and diethyl ether mixture

Quellen und Nachweise

ORD-Eintrag
ord-77d651ec5d834f7b811dbf460af1e1ff
Quelldatensatz
uspto-grants-2001_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06306852B1

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