HCID 25254645, compound → HCID 135878207, compound

Participants

Reaction Steps

5-(4-(Benzyloxy)phenyl)-3-(4-methoxyphenyl)-1,2,4-oxadiazole (50 mg, 139 μmol) and 10% Pd/C (1 mg, 10 μmol) were suspended in methanol (3.0 mL) and THF (3.0 mL). The solution was stirred in a round bottom flask fitted with a condenser and septa and placed under H2 at 55° C. for 95 hours. The solution was filtered through Celite and the solvent was removed under reduced pressure and then purified by silica gel column chromatography (EtOAc/Hex 1:2) to give the product (3 mg, 9%) as a white solid. 1H NMR (500 MHz, CDCL3) δ(ppm): 3.88 (3H, s), 5.55 (1H, s), 6.98 (2H, d, J=9.0 Hz), 7.01 (2H, d, J=8.4 Hz), 8.01 (2H, d, J=9.0 Hz), 8.12 (2H, d, J=8.2 Hz). 13C NMR (125 MHz, CDCL3) δ(ppm): 55.6 (CH3), 114.4 (CH), 116.3 (CH), 117.4, 119.7, 129.3 (CH), 130.6 (CH), 159.6, 162.1, 168.7, 175.4. MS (FAB+): 269 (MH+). HRMS for C15H12N2O3 (MH+): calculated: 269.0926; found 269.0929.

Provenance & Evidence