2-(Methoxymethyl)-2'-methylbiphenyl-4-carboxylic acid → 5-[2-(Methoxymethyl)-2'-methylbiphenyl-4-yl]-3-[3-(methylsulfonyl)phenyl]-1,2,4-oxadiazole

Participants

Reaction Steps

The title compound was obtained following procedure described for example 54 step 1 but starting from Intermediate 28 (112 mg; 0.44 mmol) and Intermediate 64 (197 mg; 0.44 mmol). Purification by column chromatography (EtOAc:cHex from 10:90 to 50:50) yielded to a colorless oil. Trituration in ACN/pentane followed by filtration gave the title compound as an off-white powder. 1H NMR (DMSO-d6, 300 MHz) δ 8.59 (t, J=1.7 Hz, 1H), 8.47 (m, 1H), 8.35 (d, J=1.7 Hz, 1H), 8.21 (m, 2H), 7.93 (t, J=8.0 Hz, 1H), 7.44 (d, J=8.0 Hz, 1H), 7.33 (m, 3H), 7.15 (d, J=7.1 Hz, 1H), 4.23 (d, J=13.8 Hz, 1H), 4.17 (d, J=13.8 Hz, 1H), 3.35 (s, 3H), 3.26 (s, 3H), 2.04 (s, 3H). LC/MS (Method B): 435.3 (M+H)+. HPLC (Method A) Rt 5.35 min (Purity: 97.6%).

Provenance & Evidence