反応 #9433

反応方程式

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

収率 66.0%

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

収率 66.0%

溶媒

DMF

反応条件

後処理

1. 1
   温度heating at 80° C.
2. 2
   温度the reaction was cooled
3. 3
   その他partitioned between water and ethyl acetate
4. 4
   洗浄the organic layer was washed with brine
5. 5
   乾燥dried (MgSO4)
6. 6
   その他evaporated
7. 7
   その他The residue was purified by column chromatography (SiO2, EtOAc:hexane 1:20)

実験手順

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%).

出典