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

HRID 646228Notes

Reaction equation

HRID 646228 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

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 687019131-[1-(2-fluoroethyl)-1H-pyrazol-4-yl]-2-[3-(2-fluoropyridin-3-yl)phenyl]ethane-1,2-dioneYield 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-f4fb423f752f4c2aa48cd817e151df2d
Source dataset
uspto-grants-2010_04
Patent number
US07705030B2

Reaction notes

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