反应详情

To N-(3-iodo-4-methylphenyl)-3-(trifluoromethyl)benzamide (400 mg, 0.99 mmol) was added (3-nitrophenyl)boronic acid (180 mg, 1.1 mmol) followed by toluene (8.2 mL), ethanol (1.1 mL), and K2CO3 (270 mg, 2.0 mmol in 1.1 mL water). The resulting mixture was degassed with N2, then tetrakis(triphenylphosphine)palladium(0) (60 mg, 0.05 mmol) was added. The mixture was degassed again, then heated under reflux condenser and N2 atmosphere at 90° C. until LCMS and TLC indicated complete reaction, typically 16 hours. The reaction was then cooled to ambient temperature and transferred to a separatory funnel and partitioned between water and EtOAc. The phases were separated and the organic phase was washed with water, then saturated aqueous NaCl. The washed organic phase was then dried (MgSO4) and evaporated to dryness to leave the crude product, which was purified by column chromatography to give the product (402 mg, 102%). 1H NMR (400 MHz, CDCl3): δ 8.23 (m, 2H), 8.12 (s, 1H), 8.07 (d, 1H), 7.88 (bs, 1H), 7.82 (d, 1H), 7.6 (m, 4H), 7.32 (d, 1H), 2.27 (s, 3H). MS (EI) m/z=401 (M+H).

1. customThe resulting mixture was degassed with N2
2. customThe mixture was degassed again
3. temperatureheated
4. temperatureunder reflux condenser
5. customat 90° C.
6. customreaction, typically 16 hours
7. customtransferred to a separatory funnel
8. custompartitioned between water and EtOAc
9. customThe phases were separated
10. washthe organic phase was washed with water
11. dry with materialThe washed organic phase was then dried (MgSO4)
12. customevaporated to dryness
13. customto leave the crude product, which
14. customwas purified by column chromatography