HCID 59631942, compound → HCID 59631919, compound

HRID 2369070Notes

Reaction equation

HRID 2369070 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([C:15]2[N:19]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[Cl:26])[N:18]=[C:17]([C:27]([F:30])([F:29])[F:28])[CH:16]=2)[CH:12]=[CH:13][CH:14]=1)C1C=CC=CC=1.[H][H]>CO.[Pd]>[Cl:26][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[N:19]1[C:15]([C:11]2[CH:10]=[C:9]([OH:8])[CH:14]=[CH:13][CH:12]=2)=[CH:16][C:17]([C:27]([F:30])([F:28])[F:29])=[N:18]1

Participants

5

Reactant 2

HCID 59631942HCID 59631942, compound2×HCID 178418361HCID 178418361, compound2×

Product 1

HCID 59631919HCID 59631919, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 887MethanolSolvent

Procedure

To a solution of 5-(3-(benzyloxy)phenyl)-1-(2-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazole in MeOH (100 mL) was added 10% palladium on carbon (1.04 g). The black suspension was shaken on the Pair hydrogenator at 40-50 psi hydrogen pressure for 5 hours. At this time the reaction was incomplete as evidenced by HPLC analysis. The reaction suspension was treated with additional Pd/C and shaken under 60 psi hydrogen pressure for an additional 16 hours. At this time HPLC showed no remaining starting 5-(3-(benzyloxy)phenyl)-1-(2-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazole. The reaction mixture was filtered through a pad of Celite that was then washed thoroughly with MeOH. The filtrate was concentrated under reduced pressure to afford 3-(1-(2-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)phenol as a brittle foam. This material was pure enough for use in subsequent transformations. MS(ES): 339 [M+H]+.

Workup

  1. filtrationThe reaction mixture was filtered through a pad of Celite that
  2. washwas then washed thoroughly with MeOH
  3. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-2dfb7162a8204347bc89f9109fe64222
Source dataset
uspto-grants-2014_04
Patent number
US08703805B2

Reaction notes

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