C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[O:19][N:18]=[C:17]([C:20]3[CH:32]=[CH:31][C:23]([O:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=4)=[CH:22][CH:21]=3)[N:16]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1.C1COCC1>CO.[Pd]>[N:26]1[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=1[O:24][C:23]1[CH:31]=[CH:32][C:20]([C:17]2[N:16]=[C:15]([C:12]3[CH:11]=[CH:10][C:9]([OH:8])=[CH:14][CH:13]=3)[O:19][N:18]=2)=[CH:21][CH:22]=12-(4-(5-(4-(Benzyloxy)phenyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyridine (310 mg, 376 μmol) was placed in a single neck round bottom flask, suspended in methanol (5.0 mL) and THF (5.0 mL) and 10% Pd/C (0.5 mg, 5.0 μmol) was added. A condenser was placed on top of the flask and then sealed. The solution was stirred under H2 at 55° C. for 22 hours. While hot, the solution was filtered through Celite washed with additional methanol and the solvent was removed under reduced pressure. The solid residue was purified by silica gel column chromatography (EtOAc/Hex 1:2) to give the product as a white solid (7 mg, 3%). 1H NMR (500 MHz, CDCL3) δ(ppm): 7.00 (2H, d, J=8.8 Hz), 7.14 (1H, d, J=8.2 Hz), 7.05 (1H, ddd, J=7.3, 5.0, 1.0 Hz), 7.32 (2H, d, J=8.8 Hz), 7.92 (1H, ddd, J=8.8, 8.2, 2.0 Hz), 8.03 (2H, d, J=8.8 Hz), 8.11 (2H, d, J=8.8 Hz), 8.21 (1H, ddd, J=5.0, 2.0, 1.0 Hz). 13C NMR (125 MHz, CDCL3) δ(ppm): 112.2 (CH), 114.1, 116.3 (CH), 119.7 (CH), 121.5 (CH), 122.4, 128.7 (CH), 130.1 (CH), 140.5 (CH), 147.6 (CH), 156.6, 162.1, 162.4 167.6, 175.5. MS (FAB+): 332 (MH+). HRMS for C19H13N3O3 (MH+): calculated: 332.1035; found 332.1049.
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