Tetrahydrofuran → HCID 135878209, compound

HRID 2167344Notes

Reaction equation

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][N:28]=[CH:27][CH:26]=4)=[CH:22][CH:21]=3)[N:16]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1.C1COCC1>CO>[N:28]1[CH:29]=[CH:30][C:25]([O:24][C:23]2[CH:22]=[CH:21][C:20]([C:17]3[N:16]=[C:15]([C:12]4[CH:13]=[CH:14][C:9]([OH:8])=[CH:10][CH:11]=4)[O:19][N:18]=3)=[CH:32][CH:31]=2)=[CH:26][CH:27]=1

Participants

Conditions

Temperature: 55 °C

Procedure

In a single neck round bottom flask fitted with a condenser, 4-(4-(5-(4-(benzyloxy)phenyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyridine (97 mg, 229 μmol) was suspended in methanol (3.0 mL) and THF (3.0 mL) 10% Pd/C (1 mg, 16 μmol) was added The reaction vessel was sealed and the solution was stirred under H2 at 55° C. for 14 hours. The hot solution was filtered through Celite and the pad was washed with methanol (20 mL). The hot solution was filtered through Celite and the pad was washed with methanol (20 mL). 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 (3 mg, 4%). 1H NMR (500 MHz, DMSO-d6) δ(ppm): 6.57 (2H, d, J=7.8 Hz), 6.84 (1H, d, J=9.0 Hz), 7.50 (2H, d, J=8.8 Hz), 7.56 (2H, d, J=8.8 Hz), 7.75 (2H, d, J=8.8 Hz), 8.08 (2H, d, J=7.8 Hz).

Workup

customIn a single neck round bottom flask fitted with a condenser
customwas sealed
filtrationThe hot solution was filtered through Celite
washthe pad was washed with methanol (20 mL)
filtrationThe hot solution was filtered through Celite
washthe pad was washed with methanol (20 mL)
customThe solvent was removed under reduced pressure the solid residue
customwas purified by silica gel column chromatography (EtOAc/Hex 1:2)

Sources & evidence

ORD record: ord-f07cfb5e1cba415eb44d3bbad9621004
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09045442B2

Reaction notes

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