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Iodine → HCID 87091918, Verbindung

HRID 1505461
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1505461
N[C:2]1[C:3]2[C:27]3([CH2:31][CH2:30][O:29][CH2:28]3)[C:26](=[O:32])[NH:25][C:4]=2[N:5]=[C:6]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[CH:14][CH:15]=3)[N:10]([CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[F:24])[N:9]=2)[N:7]=1.[I-:33].[Cs+].II.N(OCCC(C)C)=O>COCCOC.[Cu]I>[F:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[CH2:17][N:10]1[C:11]2=[N:12][CH:13]=[CH:14][CH:15]=[C:16]2[C:8]([C:6]2[N:7]=[C:2]([I:33])[C:3]3[C:27]4([CH2:31][CH2:30][O:29][CH2:28]4)[C:26](=[O:32])[NH:25][C:4]=3[N:5]=2)=[N:9]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 807IodineHCID 8053Isoamyl NitriteHCID 24601Cesium iodideHCID 56598426HCID 56598426, Verbindung

Produkt 1

HCID 87091918HCID 87091918, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
Katalysator
HCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

563 mg (1.305 mmol) of the compound obtained in Example 15A were initially charged in 1,2-dimethoxyethane (7.5 ml), and 339 mg (1.305 mmol) of caesium iodide, 165 mg (0.652 mmol) of iodine and 74 mg (0.391 mmol) of copper(I) iodide were then added. Isopentyl nitrite (1.04 ml) was then added, and the mixture was heated at 60° C. for 2 days. After cooling, the mixture was filtered, the filter cake was washed with ethyl acetate and the filtrate was washed twice with 5% strength aqueous sodium thiosulphate solution and once with saturated aqueous sodium chloride solution. The organic phase was then dried over sodium sulphate, filtered and concentrated to dryness. The residue was purified by preparative HPLC (acetonitrile/water (+0.05% formic acid) gradient). This gave 98 mg of the title compound (14% of theory).

Aufarbeitung

  1. temperatureAfter cooling
  2. filtrationthe mixture was filtered
  3. washthe filter cake was washed with ethyl acetate
  4. washthe filtrate was washed twice with 5% strength aqueous sodium thiosulphate solution and once with saturated aqueous sodium chloride solution
  5. dry with materialThe organic phase was then dried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness
  8. customThe residue was purified by preparative HPLC (acetonitrile/water (+0.05% formic acid) gradient)

Quellen und Nachweise

ORD-Eintrag
ord-0284eb83fda243a1bfcd99976ef6621f
Quelldatensatz
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09216978B2

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