Sodium Bicarbonate → HCID 86656183, compound

Participants

Reaction Conditions

Reaction Steps

To a biphasic solution of methyl 5-chloro-4-cyano-3-nitro-2-{[(trifluoromethyl)sulfonyl]oxy}benzoate (3.60 g, 9.26 mmol) and (3-fluorophenyl)boronic acid (1.42 g, 10.2 mmol) in toluene (80 mL) was added saturated NaHCO3 (80 mL) and then the reaction was bubbled with N2 to degas. Tetrakis(triphenylphosphine)palladium(0) (0.535 g, 0.463 mmol) was added. The resulting mixture was bubbled with N2 for 5 minutes and then heated at 80° C. for 2 hours. After cooling to room temperature, the mixture was diluted with ethyl acetate. The layers were separated and the aq. layer was extracted with ethyl acetate. The combined extracts were washed with brine, dried over Na2SO4, filtered, and concentrated. The resulting residue was purified on silica gel column, eluting with ethyl acetate/hexane, 0-30%, to give the desired product (1.23 g, 40%). LCMS calculated for C15H9ClFN2O4 (M+H)+: m/z=335.0; Found: 335.1. 1H NMR (CDCl3, 400 MHz) δ 8.14 (1H, s), 7.40 (1H, m), 7.20 (1H, m), 6.97 (1H, m), 6.93 (1H, m), 3.66 (3H, s) ppm.

Provenance & Evidence