Reaktion #9433

Reaktionsgleichung

5′-bromospiro{cyclohexane-1,3′-[3H]indol}-2′(1′H)-one 2′(O-benzyloxime)

sodium carbonate

3-fluoro-5-cyano-bromobenzene

potassium acetate

→

desired product

Ausbeute 66.0%

3-[1′,2′-DIHYDRO-2′-(HYDROXYIMINO)SPIRO[CYCLOHEXANE-1,3′-[3H]INDOL]-5′YL]-5-FLUOROBENZONITRILE

Ausbeute 66.0%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturheating at 80° C.
2. 2
   Temperaturthe reaction was cooled
3. 3
   Sonstigepartitioned between water and ethyl acetate
4. 4
   Waschenthe organic layer was washed with brine
5. 5
   Trocknendried (MgSO4)
6. 6
   Sonstigeevaporated
7. 7
   SonstigeThe residue was purified by column chromatography (SiO2, EtOAc:hexane 1:20)

Vorschrift

To a solution of 3-fluoro-5-cyano-bromobenzene (0.4 g, 2.0 mmol) in dry DMF (10 ml) was added diboron pinacolate ester (0.63 g, 2.5 mmol), potassium acetate (0.65 g, 6.7 mmol) and PdCl2 (dppf) (0.2 g) and the reaction was heated to 80° C. under a nitrogen atmosphere. After 8 h. from 5′-bromospiro{cyclohexane-1,3′-[3H]indol}-2′(1′H)-one 2′(O-benzyloxime) (0.2 g, 0.5 mmol), PdCl2 (dppf) (0.05 g) and sodium carbonate (1.30 g, 12.5 mmol) were added and heating at 80° C. was continued. After 8 h., the reaction was cooled and partitioned between water and ethyl acetate, the organic layer was washed with brine, dried (MgSO4) and evaporated. The residue was purified by column chromatography (SiO2, EtOAc:hexane 1:20) to give the desired product (0.14 g, 0.33 mmol, 66%).

Quelle