N-Iodosuccinimide → HCID 22050117, Verbindung

HRID 1831901Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1831901
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=2)[C:11](=[O:23])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[I:24]N1C(=O)CCC1=O>C(#N)C>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=2)[C:11](=[O:23])[C:10]=1[I:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 120273N-IodosuccinimideHCID 220502224-benzyloxy-1-(3-fluorobenzyl)-1H-pyridin-2-one

Produkt 1

HCID 22050117HCID 22050117, VerbindungAusbeute 90,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Heated a reaction mixture of 4-(benzyloxy)-1-(3-fluorobenzyl)pyridin-2(1H)-one (4.83 g, 15.6 mmol) in anhydrous acetonitrile (55 mL) and N-iodosuccinimide (NIS, 3.86 g, 17.1 mmol) under nitrogen atmosphere at 650 C for 4 h. The reaction mixture was concentrated under reduced pressure and the residue was purified by flash chromatography (silica gel) using EtOAc/hexanes (1:1 v:v). The appropriate fractions were collected according to ES MS (M+H 436) and washed with Na2SO3 to remove the color impurities. The fractions were concentrated under reduced pressure and dried in vacuo to afford the desired product (6.15 g, 90%) as a light yellow solid.

Aufarbeitung

  1. temperatureHeated
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe residue was purified by flash chromatography (silica gel)
  4. customThe appropriate fractions were collected
  5. washwashed with Na2SO3
  6. customto remove the color impurities
  7. concentrationThe fractions were concentrated under reduced pressure
  8. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-ec539c599c0d411f8ec888a3ccce30f8
Quelldatensatz
uspto-grants-2006_06
Patentnummer
US07067540B2

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