4-Chlorophenol → 3-(4-Chloro-phenoxymethyl)-1-(4-fluoro-phenyl)-5-(4-methanesulfonyl-phenyl)-2-methyl-1H-pyrrole

Participants

Reaction Steps

To a solution of 1-(4-fluorophenyl)-2-methyl-5-[4-(methylsulfonyl)phenyl]-1H-pyrrole-3-methanol (Example 21) (300 mg, 0.83 mmol), 4-chlorophenol (107 mg, 0.83 mmol), and triphenylphosphine (219 mg, 0.83 mmol) in THF (20 ml), diethyl azodicarboxylate (132 μl, 0.83 mmol) was added. The mixture was stirred at room temperature for 48 hours. The solvent was removed under reduced pressure and the crude (830 mg) was purified by chromatography (silica gel, hexane/ethyl acetate, 1/1) to give 3-[(4-chlorophenoxy)methyl]-1-(4-fluorophenyl)-2-methyl-5-[4-(methylsulfonyl)phenyl]-1H-pyrrole (29 mg, 7%): mp (DSC) 145° C. Anal Calc'd. for C25H21NSClFO3 ·0.25 H2O: C, 63.29; H, 4.57; N, 2.95. Found: C, 63.46; H, 4.57; N, 2.81.

Provenance & Evidence