Reaktion #43415

ord-c9aded2d0f824bf9b94d7c7d4dcc8f67

Reaktionsgleichung

C=C1Cn2c(=O)c(F)cc3ncc(F)c1c32
3,8-difluoro-4-methylidene-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one
CC(C)(C)O.O
tert-butanol water
O=S([O-])[O-].[Na+].[Na+]
sodium sulphite
O=c1c(F)cc2ncc(F)c3c2n1CC3(O)CO
solid
Ausbeute 97.0%
O=c1c(F)cc2ncc(F)c3c2n1CC3(O)CO
3,8-Difluoro-4-hydroxy-4-(hydroxymethyl)-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one
Ausbeute 97.0%

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    workup.ADDITIONmix alpha (4.3 g) under argon
  2. 2
    workup.STIRRINGAfter 10 minutes stirring the mixture
  3. 3
    Extraktionwas extracted with 20% methanol in dichloromethane (3×300 ml)
  4. 4
    TrocknenThe organic extracts were dried over magnesium sulphate
  5. 5
    Sonstigeevaporated

Vorschrift

A solution of 3,8-difluoro-4-methylidene-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one (631 mg, 2.9 mmol) in tert-butanol/water (30 ml/30 ml) was treated with AD mix alpha (4.3 g) under argon. After 18 hours stirring the reaction mixture was treated with saturated sodium sulphite solution (30 ml). After 10 minutes stirring the mixture was extracted with 20% methanol in dichloromethane (3×300 ml). The organic extracts were dried over magnesium sulphate and evaporated affording a white solid (710 mg, 97%).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07732460B2uspto-grants-2010_06