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

Temperature

90 °C

To a stirred solution of methyl 4-chloro-3-nitrobenzoate T20.1 (10.00 g, 46 mmol) (commercially available from Sigma-Aldrich, St. Louis, Mo., USA) in DMF (15.00 mL, 194 mmol) at 23° C. was added 2-fluoro-5-methoxyphenylboronic acid (12 g, 70 mmol) (commercially available from Sigma-Aldrich, St. Louis, Mo., USA), 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 T20.2 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 record

ord-c72ebf4d9431432ba8136ca67ae5d721

Source dataset

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08748462B2