2'-Methyl-2-[(methylsulfonyl)methyl]biphenyl-4-carboxylic acid → Methyl 2-chloro-4-(5-{2'-methyl-2-[(methylsulfonyl)methyl]biphenyl-4-yl}-1,2,4-oxadiazol-3-yl)benzoate

Participants

Reaction Steps

The title compound was prepared following procedure described for example 4, step 1, but starting from Intermediate 40 (182.62 mg; 0.60 mmol) and Intermediate 34 (114.32 mg; 0.50 mmol). The reaction mixture was filtered through a SPE NH2 column (2 g) and rinsed with ACN. The filtrate was passed through a SPE SCX column (2 g) and rinsed with ACN. After evaporation of the solvents, the crude product was purified by flash chromatography (c-hex/EtOAc: 1/1), affording the title compound. 1H NMR (CDCl3) δ 8.58 (d, J=1.7 Hz, 1H), 8.32 (d, J=1.5 Hz, 1H), 8.28 (dd, J=8.0, 1.8 Hz, 1H), 8.15 (dd, J=8.1, 1.6 Hz, 1H), 7.98 (d, J=8.1 Hz, 1H), 7.48 (d, J=7.9 Hz, 1H), 7.41-7.29 (m, 3H), 7.20 (d, J=7.3 Hz, 1H), 4.33 (d, J=13.9 Hz, 1H), 4.19 (d, J=14.0 Hz, 1H), 3.98 (s, 3H), 2.64 (s, 3H), 2.09 (s, 3H). LC/MS (Method B): 495.2 (M−H)−, 497.1 (M+H)+. HPLC (Method A) Rt 5.51 min (Purity: 99.6%).

Provenance & Evidence