Piperidine → (E)-3-(3-{6-[1-methyl-1-(methylsulfonyl)ethyl]-8-quinolinyl}phenyl)-2-[4-(methylsulfonyl)phenyl]-2-propenoic acid

Participants

Reaction Steps

A mixture of 3-{6-[1-methyl-1-(methylsulfonyl)ethyl]-8-quinolinyl}benzaldehyde from step 4 of Example 18 (2.33 g, 6.60 mmol), 4-(methylsulfonyl)phenyl acetic acid (1.71 g, 7.98 mmol) and piperidine (0.20 ml, 1.98 mmol) in 10 mL of toluene was refluxed for 2 days. The mixture was cooled to r.t., diluted with CH2Cl2, subjected to flash chromatography (CH2Cl2/EtOAc/AcOH, 50/50/1) and finally stirred with (Et2O/CH2Cl2) and isolated to give (E)-3-(3-{6-[1-methyl-1-(methylsulfonyl)ethyl]-8-quinolinyl}phenyl)-2-[4-(methylsulfonyl)phenyl]-2-propenoic acid (single isomer) as a white solid.

Provenance & Evidence