HCID 19366011, compound → HCID 178435840, compound

HRID 850086Notes

Reaction equation

HRID 850086 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]([OH:36])([C:16]([C:18]1[CH:23]=[CH:22][C:21]([C:24]2[N:28](CC3C=CC=CC=3)[N:27]=[N:26][CH:25]=2)=[CH:20][CH:19]=1)=[CH2:17])[CH2:10][N:11]1[CH:15]=[N:14][CH:13]=[N:12]1>CO.[Pd]>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]([OH:36])([CH:16]([C:18]1[CH:23]=[CH:22][C:21]([C:24]2[N:28]=[N:27][NH:26][CH:25]=2)=[CH:20][CH:19]=1)[CH3:17])[CH2:10][N:11]1[CH:15]=[N:14][CH:13]=[N:12]1

Participants

4

Reactant 1

HCID 19366011HCID 19366011, compound

Product 1

HCID 178435840HCID 178435840, compoundYield 84.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 2-(2,4-difluorophenyl)-3-(4-[1-benzyl-1,2,3-triazol-5-yl]phenyl)-1-(1,2,4-triazol-1-yl)-3-buten-2-ol(0.15 g,0.3 mmol-see Preparation 43) in methanol (100 ml) was hydrogenated at 50 psi (333 kPa) pressure over 10% palladium on charcoal (0.1 g) for 18 hours at 100° C. The cooled mixture was filtered through "Arbocel" and the filtrate was concentrated under reduced pressure. The residue was purified by flash chromatography on silica by elution with dichloromethane/methanol (19:1). Fractions containing the desired product were combined and evaporated under reduced pressure to yield the title compound as a gum (0.1 g, 81%). The product was a mixture of diastereomers by NMR.

Workup

  1. filtrationThe cooled mixture was filtered through "Arbocel"
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by flash chromatography on silica by elution with dichloromethane/methanol (19:1)
  4. additionFractions containing the desired product
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-1416a56d48dc481f9d261c8e0e17065c
Source dataset
uspto-grants-2000_01
Patent number
US06015825

Reaction notes

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