Phosphorus oxybromide → HCID 57506731, Verbindung

HRID 1945580Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1945580
[C:1]1([S:7]([N:10]2[C:18]3[CH:17]=[CH:16][N+:15]([O-])=[CH:14][C:13]=3[CH:12]=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P(Br)(Br)([Br:22])=O>C(#N)C.O1CCOCC1>[C:1]1([S:7]([N:10]2[C:18]3[CH:17]=[CH:16][N:15]=[C:14]([Br:22])[C:13]=3[CH:12]=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

5

Edukt 2

HCID 24613Phosphorus oxybromideHCID 59605785HCID 59605785, Verbindung

Produkt 1

HCID 57506731HCID 57506731, VerbindungAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A 250 mL round-bottomed flask, under nitrogen, fitted with a thermometer probe and a condenser/inert gas bubbler (via a Claisen head), was charged with a solution of 1-benzenesulfonyl-1H-pyrrolo[3,2-c]pyridine 5-oxide (3.5 g, 12.8 mmol) in acetonitrile (50 mL) and dioxane (50 mL). To this solution was added dropwise phosphorus oxybromide (12 g, 40.9 mmol) and the resulting mixture was stirred at 70° C. for 18 h. The precipitate formed was removed by filtration and washed several times with dioxane. The solution was concentrated in vacuo and partitioned between DCM, water and brine. The organic layer was isolated then dried (Na2SO4) and concentrated in vacuo. The resultant residue was purified by flash chromatography (Si—PCC, 0-20% EtOAc in cyclohexane) to give the desired product (3.1 g, 72%). 1H NMR (CDCl3, 300 MHz): δ 8.23 (d, J=5.7 Hz, 1 H); 7.94-7.85 (m, 3 H); 7.67-7.59 (m, 2 H); 7.55-7.48 (m, 2 H); 6.75 (dd, J=3.7, 0.8 Hz, 1 H).

Aufarbeitung

  1. customA 250 mL round-bottomed flask, under nitrogen, fitted with a thermometer probe
  2. customThe precipitate formed
  3. customwas removed by filtration
  4. washwashed several times with dioxane
  5. concentrationThe solution was concentrated in vacuo
  6. custompartitioned between DCM, water and brine
  7. customThe organic layer was isolated
  8. dry with materialthen dried (Na2SO4)
  9. concentrationconcentrated in vacuo
  10. customThe resultant residue was purified by flash chromatography (Si—PCC, 0-20% EtOAc in cyclohexane)

Quellen und Nachweise

ORD-Eintrag
ord-7b750460254f4fde8e3621b75267726d
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08394796B2

Notizen zur Reaktion

Wird geladen…