HCID 11603202, compound → HCID 11543755, compound

HRID 2113704Notes

Reaction equation

HRID 2113704 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([C:17]2[N:21]([C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=3)[N:20]=[CH:19][CH:18]=2)[CH:12]=[CH:13][C:14]=1[O:15][CH3:16])C1C=CC=CC=1>C(O)C>[F:28][C:25]1[CH:24]=[CH:23][C:22]([N:21]2[C:17]([C:11]3[CH:12]=[CH:13][C:14]([O:15][CH3:16])=[C:9]([OH:8])[CH:10]=3)=[CH:18][CH:19]=[N:20]2)=[CH:27][CH:26]=1

Participants

3

Reactant 1

HCID 11603202HCID 11603202, compound

Product 1

HCID 11543755HCID 11543755, compoundYield 98.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Into a 1-neck round-bottom flask was added 5-[3-(benzyloxy)-4-methoxyphenyl]-1-(4-fluorophenyl)-1H-pyrazole (3.5 g, 9.3 mmol) and 100 mL of ethanol. The flask was flushed with nitrogen for 10 minutes and 350 mg of 10% Pd/C was added. The reaction was then stirred under one atmosphere of hydrogen at room temperature overnight. The reaction was degassed under reduced pressure, flushed with argon for 5 minutes, filtered through Celite and concentrated to yield 2.6 g (98%) of 5-[1-(4-fluorophenyl)-1H-pyrazol-5-yl]-2-methoxyphenol as a grey oil. m/z 285.0 (M++1). 1H NMR (CDCl3 300 MHz) δ 3.9 (s, 3H); 5.6 (s, 1H); 6.4 (s, 1H); 6.8 (d, 1H); 7.0 (d, 2H); 7.4 (d, 2H); 7.6 (m, 2H); 7.7 (s, 1H).

Workup

  1. customThe flask was flushed with nitrogen for 10 minutes
  2. addition350 mg of 10% Pd/C was added
  3. customThe reaction was degassed under reduced pressure
  4. customflushed with argon for 5 minutes
  5. filtrationfiltered through Celite
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-38a7c3d745314c55b9a650495855eb0d
Source dataset
uspto-grants-2008_10
Patent number
US07432266B2

Reaction notes

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