HCID 68496413, compound → HCID 135949386, compound

HRID 2167322Notes

Reaction equation

HRID 2167322 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:25]=[CH:24][C:23]([O:26][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)=[CH:22][CH:21]=3)[N:16]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1>CO.C1COCC1.[Pd]>[O:26]([C:23]1[CH:22]=[CH:21][C:20]([C:17]2[N:16]=[C:15]([C:12]3[CH:13]=[CH:14][C:9]([OH:8])=[CH:10][CH:11]=3)[O:19][N:18]=2)=[CH:25][CH:24]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

5

Reactant 1

HCID 68496413HCID 68496413, compound

Product 1

HCID 135949386HCID 135949386, compoundYield 31%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
55 °C

Procedure

To 5-(4-(benzyloxy)phenyl)-3-(4-phenoxyphenyl)-1,2,4-oxadiazole (50 mg, 120 μmol) was added 10% Pd/C (1 mg, 8 μmol) and the mixture was suspended in methanol (3.0 mL) and THF (3.0 mL). The solution was stirred under H2 at 55° C. for 24 hours. The solution was filtered through Celite and the solvent was removed under reduced pressure and then purified by column chromatography EtOAc/Hex (1:6→1:4) to give the product as a white solid (12 mg, 31%). 1H NMR (500 MHz, CDCL3) δ(ppm): 5.83 (1H, bs), 6.98 (2H, d, J=8.2 Hz), 7.09 (4H, m), 7.18 (1H, t, J=7.6 Hz), 8.12 (2H, t, J=7.7 Hz), 8.12 (2H, d, J=6.8 Hz). 13C NMR (125 MHz, CDCL3) δ(ppm): 116.3 (CH), 117.2, 118.6 (CH), 119.9 (CH), 121.8, 124.4 (CH), 129.5 (CH), 130.2 (CH), 130.6 (CH), 156.4, 159.8, 160.3, 168.5, 175.7. MS (FAB+): 331 (MH+). HRMS for C20H14N2O3 (MH+): calculated: 331.1083; found 331.1056.

Workup

  1. filtrationThe solution was filtered through Celite
  2. customthe solvent was removed under reduced pressure
  3. custompurified by column chromatography EtOAc/Hex (1:6→1:4)

Sources & evidence

ORD record
ord-da4e598ccd074cb1884d0c46bd7f12c7
Source dataset
uspto-grants-2015_06
Patent number
US09045442B2

Reaction notes

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