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

HRID 33903노트

반응식

HRID 33903 반응식
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

참가 물질

4

반응물 3

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

생성물 1

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

실험 절차

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 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).

후처리

  1. temperaturethe reaction mixture heated
  2. temperatureat reflux for 18 h
  3. customThe reaction mixture was quenched with 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

출처 및 근거

ORD 기록
ord-1259400062a3441893578f2824f3665d
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07429665B2

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