Dimethylformamide → HCID 57551827, Verbindung

HRID 907333Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 907333
P(Cl)(Cl)(Cl)=O.[Br:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[C:13](=[O:17])[N:12]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:21][CH:20]=1)[CH:11]=[CH:10]2.CN([CH:32]=[O:33])C>>[Br:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[C:13](=[O:17])[N:12]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:26])=[O:27])=[CH:21][CH:20]=1)[CH:11]=[C:10]2[CH:32]=[O:33]

Komponenten

4

Edukt 3

HCID 6228Dimethylformamide2×HCID 24813Phosphorus oxychlorideHCID 575517876-Bromo-2-(4-methanesulfonyl-benzyl)-2H-isoquinolin-1-one

Produkt 1

HCID 57551827HCID 57551827, Verbindung

Versuchsvorschrift

DMF (10 mL) was cooled in an ice bath and phosphorus oxychloride (1.4 mL) added over 20 seconds. The solution was stirred for 10 minutes at room temperature then a solution of the product of step i) (2.0 g) in DMF (4 mL) was added over 5 minutes. The mixture was heated at 95° C. for 16 hours then allowed to cool and poured onto ice/water. The mixture was then extracted into ethyl acetate (100 mL) the organics combined and evaporated under reduced pressure. The residue was purified (SiO2 chromatography, eluting with 1:1 ethyl acetate:isohexane) to give the sub-titled compound (1.5 g).

Aufarbeitung

  1. temperatureThe mixture was heated at 95° C. for 16 hours
  2. temperatureto cool
  3. additionpoured onto ice/water
  4. extractionThe mixture was then extracted into ethyl acetate (100 mL) the
  5. customevaporated under reduced pressure
  6. customThe residue was purified
  7. wash(SiO2 chromatography, eluting with 1:1 ethyl acetate:isohexane)

Quellen und Nachweise

ORD-Eintrag
ord-481810dd02aa4214b9f2b4c564e2f059
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08012979B2

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