p-Toluenesulfonic acid → 2-methyl-5-[4-(methylsulfonyl)phenyl]-1-[4-(trifluoromethyl)phenyl]-1H-pyrrole

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Reaction Steps

A mixture of 1-(4-methylsulfonylphenyl)-1,4-pentanedione (Example 1, Step 2) (300 mg, 1.18 mmol), 4-(trifluoromethyl)aniline hydrochloride (257 mg, 1.3 mmol) and p-toluenesulfonic acid (30 mg) in toluene (80 ml) was heated to reflux for 20 hours. The reaction mixture was cooled, filtered and concentrated. The crude solid (560 mg) was purified by chromatography (silica gel, hexane/ethyl acetate, 7/3) to give 2-methyl-5-[4-(methylsulfonyl)phenyl]-1-[4-(trifluoromethyl)phenyl]-1H-pyrrole (351 mg, 78%) as a white solid: mp (DSC) 130° C. Anal Calc'd. for C19H16NSO2F3 : C, 60.15; H, 4.25; N, 3.69. Found: C, 60.38; H, 4.44; N, 3.67.

Provenance & Evidence