Tetrahydrofuran → Methyl 4-[5-(2,2'-dimethylbiphenyl-4-yl)-1,2,4-oxadiazol-3-yl]-3-methoxybenzoate

Participants

Reaction Conditions

Reaction Steps

The title compound was prepared following procedure described for example 43, step 1 to give 2,2′-dimethylbiphenyl-4-carbonyl chloride (0.50 mmol) as a yellow oil. The latter was dissolved in anhydrous THF (3 mL), Intermediate 47 (112.11 mg; 0.50 mmol) and DIEA (170.06 μL; 1 mmol) were added under argon. The mixture was heated in the microwave at 150° C. for 15 min. The reaction mixture was diluted in water and extracted with EtOAc, the organic phase was then washed with NH4Cl, NaHCO3 and NaCl sat. solution. The organic layer was then dried over magnesium sulfate, filtered and concentrated, the crude product was suspended in ACN, filtrated, recristalized in EtOAC and dried under vacuo, affording the title compound as a white solid. 1H NMR (DMSO-d6, 300 MHz) δ 8.15-8.12 (m, 2H), 8.06 (dd, J=7.6, 1.5 Hz, 1H), 7.77-7.72 (m, 2H), 7.38-7.27 (m, 4H), 7.14-7.11 (m, 1H), 4 (s, 3H), 3.92 (s, 3H), 2.13 (s, 3H), 2.03 (s, 3H). LC/MS (Method A): 415.3 (M+H)+. HPLC (Method A) Rt 6 min (Purity: 98.1%).

Provenance & Evidence