Diisopropylethylamine → 3-Iodo-4-methyl-N-[3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl]benzamide

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Reaction Steps

A solution of 3-iodo-4-methylbenzoic acid (1.31 g, 5 mmol) in SOCl2 (10 mL) was refluxed for 2 hrs, then evaporated in vacuo to remove residual SOCl2. The residue was dissolved in 5 mL anhydrous THF and added to a solution of DIPEA (0.77 g, 6 mmol), 3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline (1.21 g, 5 mmol) and DMAP (24 mg) in 10 mL anhydrous THF in dropwise. The result mixture was stirred at rt for 20 hrs, and evaporated in vacuo. To the residue water was added and extracted with EtOAc (50 mL×3) then CH2Cl2. The combined organic layers were evaporated in vacuo to give crude product. The crude product was triturated with CH2Cl2/EtOAc to give the title compound 2.04 g as a colorless solid (84.3%). 1H NMR (300 MHz, DMSO-d6) δ: 10.67 (1H, s), 8.46 (1H, d, J=1.5 Hz), 8.27 (1H, s), 8.21 (1H, s), 8.14 (1H, s), 7.93-7.96 (1H, dd, J=1.5 and 7.5 Hz), 7.74 (1H, s), 7.50-7.55 (2H, m), 2.46 (3H, s), 2.19 (3H, s). LCMS: m/z [M+H]+ 486.0211.

Provenance & Evidence