Cesium carbonate → HCID 66599396, compound

Participants

Reaction Conditions

Reaction Steps

4-Amino-3′-methoxybiphenyl-3-carbonitrile (4.23 g, 18.86 mmol), methyl 3-bromobenzoate (4.87 g, 22.63 mmol), palladium(II) acetate (0.212 g, 0.943 mmol), 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (1.091 g, 1.886 mmol) and cesium carbonate (8.60 g, 26.4 mmol) in a pressure vessel was flushed with nitrogen and toluene (75 mL) was added. The mixture was heated at 100° C. overnight. The reaction mixture was filtered and the solid was washed with DCM (2×20 mL). The filtrate was concentrated and the product was purified by flash-chromatography eluting with hexane containing 5 to 20% ethyl acetate. This gave 5.14 g (65% yield) of methyl 3-(3-cyano-3′-methoxybiphenyl-4-ylamino)benzoate. MS (ESI) m/z 359.1 (M+H). 1H NMR (CDCl3) δ ppm 7.88 (1H, s), 7.77 (1H, d, J=7.63 Hz), 7.72 (1H, d, J=2.44 Hz), 7.61 (1H, dd, J=8.70, 2.29 Hz), 7.42 (1H, t, J=7.93 Hz), 7.30-7.39 (2H, m), 7.27 (1H, d, J=8.85 Hz), 7.08 (1H, d, J=7.93 Hz), 7.02 (1H, t, J=2.14 Hz), 6.88 (1H, dd, J=8.24, 2.44 Hz), 6.56 (1H, s), 3.91 (3H, s), 3.85 (3H, s).

Provenance & Evidence