反应详情

温度

150 °C

The following reaction was split into two batches with half the amounts: methyl 3-cyano-4-{[(trifluoromethyl)sulfonyl]oxy}benzoate (D25) (1.5 g, 4.85 mmol), phenylboronic acid (1.183 g, 9.70 mmol), potassium carbonate (2.011 g, 14.55 mmol) and palladium tetrakistriphenylphosphine(0) (0.561 g, 0.485 mmol) were taken up in DMF (24 ml) and the mixture heated in the microwave for 30 min at 150° C. The two reactions were combined and diluted with ethyl acetate (50 mL) and the mixture filtered through kieselguhr to remove palladium residues. The filtrate was concentrated in vacuo to reduce the amount of DMF and then the residue partitioned between saturated aqueous sodium bicarbonate (50 mL) and ethyl acetate (50 mL). The organic phase was washed with further sodium bicarbonate (50 mL) and then water (50 mL) before it was dried (MgSO4), filtered and the solvent removed in vacuo. The brown solid was purified by silica chromatography, eluting 0-25% EtOAc in iso-hexane over 35 minutes to give the title compound as a white solid (935 mg, 3.94 mmol). δH (d6-DMSO, 400 MHz): 8.42 (1H, d), 8.29 (1H, dd), 7.81 (1H, d), 7.65 (2H, m), 7.60-7.50 (3H, m), 3.92 (3H, s). MS (ES): no mass ion observed.

1. customThe following reaction
2. customwas split into two batches with half the amounts
3. filtrationthe mixture filtered through kieselguhr
4. customto remove palladium residues
5. concentrationThe filtrate was concentrated in vacuo
6. customthe residue partitioned between saturated aqueous sodium bicarbonate (50 mL) and ethyl acetate (50 mL)
7. washThe organic phase was washed with further sodium bicarbonate (50 mL)
8. dry with materialwater (50 mL) before it was dried (MgSO4)
9. filtrationfiltered
10. customthe solvent removed in vacuo
11. customThe brown solid was purified by silica chromatography
12. washeluting 0-25% EtOAc in iso-hexane over 35 minutes