Dichloromethane → 4'-Amino-3-fluoro-3'-nitro-[1,1'-biphenyl]-4-carbonitrile

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-bromo-2-nitroaniline (5.02 g, 23.1 mmol), 4-cyano-3-fluorophenylboronic acid (3.62 g, 21.9 mmol), and sodium carbonate (6.1 g, 58 mmol) in water (10 mL) and tetrahydrofuran (35 mL) was sparged with nitrogen for 10 minutes. To this was added [1,1-bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with dichloromethane (1:1) (0.42 g, 0.51 mmol). The reaction mixture was heated at 65° C. for 6 hours. The mixture was allowed to cool, concentrated in vacuo, diluted with ethyl acetate, washed with saturated aqueous sodium hydrogen carbonate, water and brine. The organic layer was dried over anhydrous magnesium sulphate, filtered, and concentrated in vacuo. The residue was purified using silica gel column chromatography eluting with a 0-100% ethyl acetate/hexanes gradient to afford the title compound (3.64 g, 65%) as a yellow solid.

Provenance & Evidence