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Propargyl alcohol → HCID 178522909, Verbindung

HRID 2289940
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2289940
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][C:10]([C:12]2[CH:13]=[N:14][C:15]3[C:20]([C:21]=2[OH:22])=[CH:19][C:18](I)=[CH:17][C:16]=3[F:24])=[O:11])=[CH:4][CH:3]=1.[CH2:25]([OH:28])[C:26]#[CH:27]>C(NCC)C.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][C:10]([C:12]2[CH:13]=[N:14][C:15]3[C:20]([C:21]=2[OH:22])=[CH:19][C:18]([C:27]#[C:26][CH2:25][OH:28])=[CH:17][C:16]=3[F:24])=[O:11])=[CH:4][CH:3]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 2

HCID 7859Propargyl alcoholHCID 178522917HCID 178522917, Verbindung

Produkt 1

HCID 178522909HCID 178522909, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418476HCID 178418476, VerbindungKatalysator
HCID 8021DiethylamineLösungsmittel

Versuchsvorschrift

To a mixture of N-[(4-chlorophenyl)methyl]-8-fluoro-4-hydroxy-6-iodo-3-quinolinecarboxamide of Example 5 (0.466 g) in 15 mL diethylamine is added CuI (0.010 g) and (Ph3P)2PdCl2 (0.035 g). Propargyl alcohol (0.058 mL) is then added and the reaction is stirred overnight at room temperature. The diethylamine is removed in vacuo. The residue is partitioned between EtOAc and water. The insoluble material is filtered off and saved. The organic layer is washed with brine, dried and condensed. The residue is combined with the insoluble material and adsorbed onto silica and chromatographed, eluting with 3% MeOH/CH2Cl2. Fractions homogeneous by TLC are combined and condensed to yield 0.192 g of the desired product as a tan solid.

Aufarbeitung

  1. customThe diethylamine is removed in vacuo
  2. customThe residue is partitioned between EtOAc and water
  3. filtrationThe insoluble material is filtered off
  4. washThe organic layer is washed with brine
  5. customdried
  6. customcondensed
  7. customchromatographed
  8. washeluting with 3% MeOH/CH2Cl2
  9. customcondensed

Quellen und Nachweise

ORD-Eintrag
ord-9a3c89c4247f42ab830cae5cd4721ac3
Quelldatensatz
uspto-grants-2000_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06093732

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