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Water → 1-[1-(2-fluoroethyl)-1H-pyrazol-4-yl]-2-[3-(2-fluoropyridin-3-yl)phenyl]ethane-1,2-dione

HRID 2220450
Notes
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Reaction equation

HRID 2220450 reaction equation
[F:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]#[C:15][C:16]3[CH:17]=[N:18][N:19]([CH2:21][CH2:22][F:23])[CH:20]=3)[CH:9]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.C([O-])(O)=[O:25].[Na+].[O-]S([O-])(=O)=O.[Mg+2].[Mn]([O-])(=O)(=O)=O.[K+].[OH2:41]>CC(C)=O>[F:23][CH2:22][CH2:21][N:19]1[CH:20]=[C:16]([C:15](=[O:25])[C:14]([C:10]2[CH:11]=[CH:12][CH:13]=[C:8]([C:7]3[C:2]([F:1])=[N:3][CH:4]=[CH:5][CH:6]=3)[CH:9]=2)=[O:41])[CH:17]=[N:18]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 962WaterHCID 24083Sulfuric acid magnesium salt (1:1)HCID 516875Potassium PermanganateHCID 516892Sodium BicarbonateHCID 597726592-fluoro-3-(3-{[1-(2-fluoroethyl)-1H-pyrazol-4-yl]ethynyl}phenyl)pyridine

Product 1

HCID 68701913
1-[1-(2-fluoroethyl)-1H-pyrazol-4-yl]-2-[3-(2-fluoropyridin-3-yl)phenyl]ethane-1,2-dione
Yield 62%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 2-fluoro-3-(3-{[1-(2-fluoroethyl)-1H-pyrazol-4-yl]ethynyl}phenyl)pyridine (140 mg, 0.45 mmol) in acetone (7 mL) is added a warm (−40° C.) solution of NaHCO3 (23 mg, 0.27 mmol) and MgSO4 (82 mg, 0.68 mmol) in H2O (7 mL) followed by the addition of solid potassium permanganate (156 mg, 0.99 mmol) in one portion. After stirring at room temperature for 30 minutes, the reaction mixture is extracted with Et2O/hexane (1/1) until no product left in aqueous layer. The combined organic extracts are dried (MgSO4) and concentrated to dryness to afford 1-[1-(2-fluoroethyl)-1H-pyrazol-4-yl]-2-[3-(2-fluoropyridin-3-yl)phenyl]ethane-1,2-dione (95 mg, 62%) as an oil. MS (+) ES: 342 (M+H)+.

Workup

  1. extractionthe reaction mixture is extracted with Et2O/hexane (1/1) until no product
  2. waitleft in aqueous layer
  3. dry with materialThe combined organic extracts are dried (MgSO4)
  4. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-9a33f42b598145cea56845f605f32165
Source dataset
uspto-grants-2008_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07417047B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes