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Selectfluor → 3-(4-Fluoro-1-phenyl-1h-pyrazol-5-yl)-1-[3-(trifluoromethyl)phenyl]pyridazin-4(1h)-one

HRID 1624769
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HRID 1624769 반응식
[C:1]1([N:7]2[C:11]([C:12]3[C:17](=[O:18])[CH:16]=[CH:15][N:14]([C:19]4[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[CH:20]=4)[N:13]=3)=[CH:10][CH:9]=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[B-](F)(F)(F)[F:30].[B-](F)(F)(F)F.C1[N+]2(CCl)CC[N+](F)(CC2)C1>CC#N.[Cl-].[Na+].O>[F:30][C:10]1[CH:9]=[N:8][N:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:11]=1[C:12]1[C:17](=[O:18])[CH:16]=[CH:15][N:14]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:27])([F:26])[F:28])[CH:20]=2)[N:13]=1
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참가 물질

5

반응물 2

HCID 2724933Selectfluor5회HCID 462198193-(1-Phenyl-1h-Pyrazol-5-Yl)-1-[3-(Trifluoromethyl)phenyl]pyridazin-4(1h)-One

생성물 1

HCID 580722333-(4-Fluoro-1-phenyl-1h-pyrazol-5-yl)-1-[3-(trifluoromethyl)phenyl]pyridazin-4(1h)-one수율 23%

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 57417360
Sodium chloride; water
용매

실험 절차

A mixture of 3-(1-phenyl-1H-pyrazol-5-yl)-1-[3-(trifluoromethyl)phenyl]pyridazin-4(1H)-one (49.0 mg, 0.128 mmol) and selectfluor (45.4 mg, 0.128 mmol) in MeCN (1 mL) was stirred at room temperature for 6 days. To the mixture was added selectfluor (45.4 mg, 0.128 mmol) at room temperature. The mixture was stirred at room temperature for 1 day. To the mixture was added selectfluor (45.4 mg, 0.128 mmol) at room temperature. The mixture was stirred at room temperature for 1 day. To the mixture was added selectfluor (45.4 mg, 0.128 mmol) at room temperature. The mixture was stirred at room temperature for 1 day. To the mixture was added selectfluor (272 mg, 0.768 mmol) at room temperature. The mixture was stirred at room temperature for 3 days. The mixture was diluted with brine, extracted with AcOEt, dried over MgSO4, filtered, concentrated in vacuo, purified by column chromatography on silica gel (hexane/AcOEt=50/50 to 0/100) and crystallized with AcOEt/hexane to yield the title compound (11.7 mg, 23% yield) as a pale yellow solid: mp 156-158° C. 1H NMR (DMSO-d6, 300 MHz): δ ppm 6.67 (1H, d, J=8.2 Hz), 7.33-7.50 (5H, m), 7.63-7.83 (4H, m), 7.97 (1H, d, J=4.1 Hz), 8.96 (1H, d, J=8.0 Hz).

후처리

  1. stirringThe mixture was stirred at room temperature for 1 day
  2. stirringThe mixture was stirred at room temperature for 1 day
  3. stirringThe mixture was stirred at room temperature for 1 day
  4. stirringThe mixture was stirred at room temperature for 3 days
  5. extractionextracted with AcOEt
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. custompurified by column chromatography on silica gel (hexane/AcOEt=50/50 to 0/100)
  10. customcrystallized with AcOEt/hexane

출처 및 근거

ORD 기록
ord-c355f13ce3f8491fb40d4cf249f02eec
출처 데이터셋
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08778944B2

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