Cesium fluoride → HCID 66604498, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-amino-3,5-dibromobenzonitrile (250 mg, 0.906 mmol), 4-methoxyphenylboronic acid (330 mg, 2.17 mmol), tetrakis(triphenylphosphine)-palladium(0) (52 mg, 0.045 mmol) and cesium fluoride (661 mg, 4.35 mmol) was placed in a vial and flushed with nitrogen. Dimethoxyethane (4.5 mL) was added and the reaction was heated at 80° C. for 7 hr. After cooling to room temperature, the reaction was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution. The organic phase was separated, washed with saturated aqueous sodium bicarbonate solution, brine, and then dried with sodium sulfate. Removal of the solvent followed by silica gel radial chromatography (step gradient elution with hexane containing 0 to 20% ethyl acetate) afforded 4′-amino-4,4″-dimethoxy-[1,1′:3′,1″-terphenyl]-5′-carbonitrile (267 mg, 89% yield) as an oil. MS (ESI) m/z 331.1 (M+H). 1H NMR (CDCl3) δ ppm 7.54 (1H, d, J=2.14 Hz), 7.46 (1H, d, J=2.14 Hz), 7.42 (2H, d, J=8.55 Hz), 7.36 (2H, d, J=8.55 Hz), 7.01 (2H, d, J=8.55 Hz), 6.94 (2H, d, J=8.55 Hz), 4.50 (2H, s), 3.86 (3H, s), 3.83 (3H, s).

Provenance & Evidence