Trifluoroacetic acid → 3-Fluoro4-[4-pyridin-4-yl-1-(2,2,2-trifluoro-ethyl)-1H-pyrazol-3-yl]-phenol

HRID 1170343Notes

Reaction equation

HRID 1170343 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:19]([C:20]3[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=3)=[CH:18][N:17]([CH2:26][C:27]([F:30])([F:29])[F:28])[N:16]=2)=[C:11]([F:31])[CH:10]=1)C1C=CC=CC=1.FC(F)(F)C(O)=O.C1(OC)C=CC=CC=1>>[F:31][C:11]1[CH:10]=[C:9]([OH:8])[CH:14]=[CH:13][C:12]=1[C:15]1[C:19]([C:20]2[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=2)=[CH:18][N:17]([CH2:26][C:27]([F:28])([F:29])[F:30])[N:16]=1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 685753054-[3-(4-Benzyloxy-2-fluoro-phenyl)-1-(2,2,2-trifluoroethyl)-1H-pyrazol-4-yl]-pyridine

Product 1

HCID 1363758193-Fluoro4-[4-pyridin-4-yl-1-(2,2,2-trifluoro-ethyl)-1H-pyrazol-3-yl]-phenolYield 77.7%

Procedure

To 4-[3-(4-Benzyloxy-2-fluoro-phenyl)-1-(2,2,2-trifluoro-ethyl)-1H-pyrazol-4-yl]-pyridine (900 mg) was added trifluoroacetic acid (5.25 ml) and anisole (1.15 ml) and the reaction mixture heated at reflux for 18 h. The reaction mixture was quenched with 1N NaOH, extracted 3× tetrahydrofuran, dried magnesium sulfate, filtered and concentrated. Purification via Biotage MPLC eluting with 5% methanol/1% ammonium hydroxide/ethyl acetate provided the title compound (552 mg). MS: (M+H m/z=338.2).

Workup

  1. temperaturethe reaction mixture heated
  2. temperatureat reflux for 18 h
  3. customThe reaction mixture was quenched with 1N NaOH
  4. extractionextracted 3× tetrahydrofuran, dried magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification via Biotage MPLC
  8. washeluting with 5% methanol/1% ammonium hydroxide/ethyl acetate

Sources & evidence

ORD record
ord-6c47bb6a3a5e423ab302516a26eaf39b
Source dataset
uspto-grants-2010_11
Patent number
US07825254B2

Reaction notes

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