HCID 58128597, compound → HCID 12463129, compound

HRID 1798814Notes

Reaction equation

HRID 1798814 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[N:19]=[CH:18][CH:17]=[N:16]2)=[CH:11][CH:10]=1)C1C=CC=CC=1>C(OCC)(=O)C.C(O)C.[OH-].[Pd+2].[OH-]>[N:16]1[N:15]([C:12]2[CH:11]=[CH:10][C:9]([OH:8])=[CH:14][CH:13]=2)[N:19]=[CH:18][CH:17]=1

Participants

5

Reactant 1

HCID 58128597HCID 58128597, compound

Product 1

HCID 12463129HCID 12463129, compound

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-[4-(benzyloxy)phenyl]-2H-1,2,3-triazole (400 mg, 1.6 mmol) was dissolved in 3.2 mL of a mixture of ethyl acetate and ethanol (1:1). The solution was degassed and purged with nitrogen. Palladium hydroxide (20% w/w on carbon, 110 mg, 0.16 mmol) was added and the reaction was degassed and purged with hydrogen three times. The hydrogenation was continued at room temperature under a hydrogen balloon for 1 hour. The catalyst was removed by filtration through a plug of silica gel, which was washed thoroughly with acetone. Concentration afforded the product as white solid. LRMS calc: 161.1; obs: 162.2 (M+1).

Workup

  1. customThe solution was degassed
  2. custompurged with nitrogen
  3. customthe reaction was degassed
  4. custompurged with hydrogen three times
  5. customwas continued at room temperature under a hydrogen
  6. customfor 1 hour
  7. customThe catalyst was removed by filtration through a plug of silica gel, which
  8. washwas washed thoroughly with acetone
  9. concentrationConcentration

Sources & evidence

ORD record
ord-c1abe65c772b4bf8b0673628af189edc
Source dataset
uspto-grants-2013_01
Patent number
US08343990B2

Reaction notes

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