反应详情

A solution of 3-iodo-4-methylbenzoic acid (0.26 g, 1 mmol) in SOCl2 (5 mL) was refluxed for 3 hrs, then evaporated in vacuo to remove residual SOCl2. The residue was dissolved in 5 mL anhydrous THF and added to a solution of triethylamine (0.12 g, 1 mmol), 4-(4-methyl-1H-imidazol-1-yl)-3-(trifluoromethyl)aniline (0.24 g, 1 mmol) and DMAP (12 mg) in 5 mL anhydrous THF in dropwise. The result mixture was stirred at rt for 40 hrs, and evaporated in vacuo. To the residue water was added and extracted with EtOAc (20 mL×3), the organic layer was washed with brine, dried with Na2SO4, after filtration, the filtrate was purified by chromatography on silica gel (CH2Cl2/CH3OH 97:3) to give 0.4 g crude product. The crude product was triturated with PE/EtOAc to give the title compound 0.35 g as pale yellow solid (72.2%). 1H NMR (300 MHz, CDCl3) δ: 8.91 (1H, s), 8.37 (1H, s), 8.08-8.12 (2H, m), 7.86-7.83 (1H, d, J=8.4 Hz), 7.54 (1H, s), 7.34-7.36 (2H, m), 6.84 (1H, s), 2.50 (3H, s), 2.29 (3H, s). LCMS: m/z [M+H]+ 486.0493.

1. customevaporated in vacuo
2. customto remove residual SOCl2
3. dissolutionThe residue was dissolved in 5 mL anhydrous THF
4. customevaporated in vacuo
5. additionTo the residue water was added
6. extractionextracted with EtOAc (20 mL×3)
7. washthe organic layer was washed with brine
8. dry with materialdried with Na2SO4
9. filtrationafter filtration
10. customthe filtrate was purified by chromatography on silica gel (CH2Cl2/CH3OH 97:3)
11. customto give 0.4 g crude product
12. customThe crude product was triturated with PE/EtOAc