Réaction #9433

Équation de réaction

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

Rendement 66.0%

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

Rendement 66.0%

Solvants

DMF

Conditions de réaction

Traitement

1. 1
   Températureheating at 80° C.
2. 2
   Températurethe reaction was cooled
3. 3
   Autrepartitioned between water and ethyl acetate
4. 4
   Lavagethe organic layer was washed with brine
5. 5
   Séchagedried (MgSO4)
6. 6
   Autreevaporated
7. 7
   AutreThe residue was purified by column chromatography (SiO2, EtOAc:hexane 1:20)

Mode opératoire

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%).

Source