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

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).

1. customThe reaction vessel was purged
2. customflushed with nitrogen three times
3. customThe reaction mixture was microwaved at 150° C. for 60 minutes
4. filtrationAfter 30 minutes the mixture was filtered
5. customthe filtrate was partitioned between water and ethyl acetate
6. extractionExtracted with ethyl acetate (3×20 mL)
7. washwashed with brine
8. dry with materialdried over magnesium sulfate
9. concentrationconcentrated
10. customPurified by MPLC with a gradient of 20 to 50% EtOAc in CH2Cl2

ORD-Eintrag

ord-2749dc371527437e9924f4eb2acea80b

Quelldatensatz

uspto-grants-2013_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08524900B2