Sodium Carbonate → HCID 69546259, Verbindung

Temperatur

80 °C

A vigorously stirred suspension of the product of step C (1.00 g, 2.48 mmol), 4-chlorophenylboronic acid (0.427 g, 2.73 mmol) and [1,1′-bis(diphenylphosphino)-ferrocene)dichloropalladium(II) (0.102 g, 0.124 mmol) in toluene/ethanol (3:2; 24.0 mL) was degassed via three vacuum/nitrogen ingress cycles and then heated to approximately 80° C. Aqueous 2 M sodium carbonate (3.10 mL, 6.20 mmol) was added dropwise via syringe and the resulting mixture maintained at reflux overnight. After cooling to ambient temperature, the reaction mixture was diluted with ethyl acetate and filtered through celite®. The filtrate was poured into water and extracted three times with ethyl acetate. The combined organic extracts were washed with brine, dried (MgSO4) and concentrated in vacuo. Purification of the residue by medium pressure liquid chromatography on silica gel (gradient elution; 0–15% ethyl acetate/hexanes as eluent) furnished the title compound as a colorless oil (0.828 g).

1. customwas degassed via three vacuum/nitrogen ingress cycles
2. temperaturethe resulting mixture maintained
3. temperatureat reflux overnight
4. temperatureAfter cooling to ambient temperature
5. filtrationfiltered through celite®
6. additionThe filtrate was poured into water
7. extractionextracted three times with ethyl acetate
8. washThe combined organic extracts were washed with brine
9. dry with materialdried (MgSO4)
10. concentrationconcentrated in vacuo
11. customPurification of the residue by medium pressure liquid chromatography on silica gel (gradient elution; 0–15% ethyl acetate/hexanes as eluent)

ORD-Eintrag

ord-c528eac3e5104205a8f4c2533514739f

Quelldatensatz

uspto-grants-2006_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07015235B2