Water → 5-Hydroxy-3-(1-phenyl-1H-pyrazol-5-yl)-1-[3-(trifluoromethyl)phenyl]pyridazin-4(1H)-one

HRID 1407280ノート

反応式

HRID 1407280 の反応式
C[Si](Cl)(C)C.[Na+].[I-].C[O:9][C:10]1[C:11](=[O:37])[C:12]([C:26]2[N:30]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[N:29]=[CH:28][CH:27]=2)=[N:13][N:14]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=2)[CH:15]=1.O>CC#N>[OH:9][C:10]1[C:11](=[O:37])[C:12]([C:26]2[N:30]([C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)[N:29]=[CH:28][CH:27]=2)=[N:13][N:14]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:23])([F:25])[F:24])[CH:17]=2)[CH:15]=1

参加物

6

反応物 4

HCID 962WaterHCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 594361955-Methoxy-3-(1-Phenyl-1h-Pyrazol-5-Yl)-1-[3-(Trifluoromethyl)phenyl]pyridazin-4(1h)-One

生成物 1

HCID 594362225-Hydroxy-3-(1-phenyl-1H-pyrazol-5-yl)-1-[3-(trifluoromethyl)phenyl]pyridazin-4(1H)-one収率 84.4%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

TMSCl (3.17 mL, 25 mmol) was added at room temperature to a solution of NaI (3.75 g, 25 mmol) in CH3CN (150 mL). After stirring for 30 min, 5-methoxy-3-(1-phenyl-1H-pyrazol-5-yl)-1-[3-(trifluoromethyl)phenyl]pyridazin-4(1H)-one (2.06 g, 5 mmol) was added to the resulting suspension. The mixture was stirred for 30 min at room temperature and then refluxed for 1 h. After cooling to room temperature, the reaction mixture was poured into water and extracted with AcOEt. The extract was washed with brine, dried over MgSO4, and concentrated under reduced pressure. The residue was washed with hexane/AcOEt (1/1) and recrystallized from MeOH/H2O to give the title compound (1.68 g, 84% yield) as a colorless powder: mp 246-248° C.; 1H NMR (300 MHz, DMSO-d6): δ ppm 7.17 (1H, d, J=1.9 Hz), 7.33-7.46 (5H, m), 7.53-7.64 (3H, m), 7.71 (1H, d, J=7.5 Hz), 7.83 (1H, d, J=1.9 Hz), 8.83 (1H, s). Anal. Calcd for C20H13F3N4O2: C, 60.30; H, 3.29; N, 14.07. Found: C, 60.09; H, 3.33; N, 14.02.

後処理

  1. stirringThe mixture was stirred for 30 min at room temperature
  2. temperaturerefluxed for 1 h
  3. extractionextracted with AcOEt
  4. washThe extract was washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. washThe residue was washed with hexane/AcOEt (1/1)
  8. customrecrystallized from MeOH/H2O

出典と根拠

ORDレコード
ord-a7f289ab4a70426cb60b7246195fa843
出典データセット
uspto-grants-2014_12
特許番号
US08916566B2

反応ノート

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