تفاعل #9433

معادلة التفاعل

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

المردود 66.0%

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

المردود 66.0%

المذيبات

DMF

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةheating at 80° C.
2. 2
   درجة الحرارةthe reaction was cooled
3. 3
   أخرىpartitioned between water and ethyl acetate
4. 4
   غسيلthe organic layer was washed with brine
5. 5
   تجفيفdried (MgSO4)
6. 6
   أخرىevaporated
7. 7
   أخرىThe residue was purified by column chromatography (SiO2, EtOAc:hexane 1:20)

الإجراء التجريبي

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%).

المصدر