反应详情

2-Bromo-5-cyano-terephthalic acid dimethyl ester (620 mg, 2.1 mmol), 2-fluoro-4-trimethylsilanyl-phenylamine (419 mg, 2.3 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (62 mg, 0.10 mmol), potassium phosphate (486 mg, 2.30 mmol) and tris(dibenzylideneacetone)dipalladium (0) (29 mg, 0.05 mmol) were suspended in dioxane (20 ml) and the resultant mixture purged with argon. The reaction mixture was heated at reflux for 16 hours. The reaction was quenched by the addition of saturated aqueous ammonium chloride solution (20 ml) and the resultant mixture extracted with ethyl acetate (3×20 mL). The combined organic fractions were washed with brine (20 ml), dried (MgSO4) and concentrated in vacuo. The resultant residue was subjected to flash chromatography (SiO2, gradient 0-40% ethyl acetate in cyclohexane) to yield the title compound as a brown solid (0.5 g, 60%). LCMS (Method B): RT=4.74 min, M+H+=401.

1. customthe resultant mixture purged with argon
2. temperatureThe reaction mixture was heated
3. temperatureat reflux for 16 hours
4. customThe reaction was quenched by the addition of saturated aqueous ammonium chloride solution (20 ml)
5. extractionthe resultant mixture extracted with ethyl acetate (3×20 mL)
6. washThe combined organic fractions were washed with brine (20 ml)
7. dry with materialdried (MgSO4)
8. concentrationconcentrated in vacuo