Dimethylformamide → Methyl 2'-fluoro-5'-(methyloxy)-2-nitro-1,1'-biphenyl-4-carboxylate

Temperatur

90 °C

To a stirred solution of methyl 4-chloro-3-nitrobenzoate T10.1 (10.00 g, 46 mmol) (commercially available from Aldrich) in DMF (15.00 mL, 194 mmol) at 23° C. was added 2-fluoro-5-methoxyphenylboronic acid (12 g, 70 mmol) (commercially available from Aldrich), and potassium carbonate (19 g, 139 mmol). Tetrakis(triphenylphosphine)palladium (2.1 g, 1.9 mmol) was then added to the mixture, and the mixture was heated at 90° C. for 18 hours. The mixture was then cooled to room temperature, diluted with brine and extracted three times with EtOAc. After drying over anhydrous magnesium sulfate and filtering, the organic solvent was removed under reduced pressure and the product was purified on silica gel (0-40% EtOAc in hexanes) to yield T10.2 as a colorless oil (14.00 g, 99% yield).

1. temperatureThe mixture was then cooled to room temperature
2. extractionextracted three times with EtOAc
3. dry with materialAfter drying over anhydrous magnesium sulfate
4. filtrationfiltering
5. customthe organic solvent was removed under reduced pressure
6. customthe product was purified on silica gel (0-40% EtOAc in hexanes)

ORD-Eintrag

ord-e596a1f3d20b4a33bef55ad0b50e792e

Quelldatensatz

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08450522B2