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

HRID 1170343ノート

反応式

HRID 1170343 の反応式
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

参加物

4

反応物 3

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

生成物 1

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

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-6c47bb6a3a5e423ab302516a26eaf39b
出典データセット
uspto-grants-2010_11
特許番号
US07825254B2

反応ノート

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