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

HRID 1170343노트

반응식

HRID 1170343 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 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 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-6c47bb6a3a5e423ab302516a26eaf39b
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07825254B2

반응 노트

불러오는 중…