Reacción #68460

Ecuación de reacción

4-chloro-7-methoxyquinoline

tri-t-butylphosphonium tetrafluoroborate

3-ethoxy-3-oxopropylzinc bromide

THF

→

Ethyl 3-(7-methoxyquinolin-4-yl)propanoate

Disolventes

ammonium hydroxide

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe reaction vessel was purged
2. 2
   Otroflushed with nitrogen three times
3. 3
   OtroThe reaction mixture was microwaved at 150° C. for 60 minutes
4. 4
   FiltraciónAfter 30 minutes the mixture was filtered
5. 5
   Otrothe filtrate was partitioned between water and ethyl acetate
6. 6
   ExtracciónExtracted with ethyl acetate (3×20 mL)
7. 7
   Lavadowashed with brine
8. 8
   Secadodried over magnesium sulfate
9. 9
   Concentraciónconcentrated
10. 10
    OtroPurified by MPLC with a gradient of 20 to 50% EtOAc in CH2Cl2

Procedimiento

4-chloro-7-methoxyquinoline (0.35 g, 2 mmol), tri-t-butylphosphonium tetrafluoroborate (0.05 g, 0.2 mmol), and tris(dibenzylideneacetone)dipalladium (0) (0.08 g, 0.09 mmol) were combined. The reaction vessel was purged and flushed with nitrogen three times, followed by addition of 3-ethoxy-3-oxopropylzinc bromide in THF (10 mL, 5 mmol, 0.5 M). The reaction mixture was microwaved at 150° C. for 60 minutes. Upon completion, ammonium hydroxide (10 mL) was added. After 30 minutes the mixture was filtered and the filtrate was partitioned between water and ethyl acetate. Extracted with ethyl acetate (3×20 mL). The organic layers were combined, washed with brine, dried over magnesium sulfate, and concentrated. Purified by MPLC with a gradient of 20 to 50% EtOAc in CH2Cl2. (ESI, pos. ion) m/z: 354.1 (M+H).

Fuente