HCID 59533947, compound → HCID 135878213, compound

HRID 2167326Notes

Reaction equation

HRID 2167326 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][CH:23]=[CH:22][CH:21]=3)[N:16]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1>CO.C1COCC1.[Pd]>[C:20]1([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][CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 1

HCID 59533947HCID 59533947, compound

Product 1

HCID 135878213HCID 135878213, compoundYield 11%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 5-(4-(benzyloxy)phenyl)-3-phenyl-1,2,4-oxadiazole (90 mg, 0.27 mmol) and 10% Pd/C (2 mg, 7 μmol) in methanol (3.0 mL) and THF (3.0 mL) was stirred in a single necked round bottom flask fitted with a condenser under an atmosphere of hydrogen at 55° C. for 72 hours. The solution was filtered through Celite and the solvent was removed under reduced pressure and then purified by column chromatography (EtOAc/Hex 1:2) to give the product (7 mg, 11%) as a white solid. 1H NMR (500 MHz, CDCL3) δ(ppm): 6.86 (2H, d, J=8.8 Hz), 6.99 (2H, d, J=9.2 Hz), 8.01 (2H, d, J=8.8 Hz), 8.05 (2H, d, J=9.2 Hz).

Workup

  1. customfitted with a condenser under an atmosphere of hydrogen at 55° C. for 72 hours
  2. filtrationThe solution was filtered through Celite
  3. customthe solvent was removed under reduced pressure
  4. custompurified by column chromatography (EtOAc/Hex 1:2)

Sources & evidence

ORD record
ord-6805472446d44b8881a05fe1956140cd
Source dataset
uspto-grants-2015_06
Patent number
US09045442B2

Reaction notes

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