Hydrogen Peroxide → 5-(2-chloro-4-fluoro-5-(3-fluoropyridin-2-yl)benzamido)-1-phenyl-1H-pyrazole-3-carboxamide

HRID 522091Notes

Reaction equation

HRID 522091 reaction equation
[Cl:1][C:2]1[CH:23]=[C:22]([F:24])[C:21]([C:25]2[C:30]([F:31])=[CH:29][CH:28]=[CH:27][N:26]=2)=[CH:20][C:3]=1[C:4]([NH:6][C:7]1[N:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:10]=[C:9]([C:18]#[N:19])[CH:8]=1)=[O:5].C([O-])([O-])=[O:33].[K+].[K+].OO>CS(C)=O>[Cl:1][C:2]1[CH:23]=[C:22]([F:24])[C:21]([C:25]2[C:30]([F:31])=[CH:29][CH:28]=[CH:27][N:26]=2)=[CH:20][C:3]=1[C:4]([NH:6][C:7]1[N:11]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:10]=[C:9]([C:18]([NH2:19])=[O:33])[CH:8]=1)=[O:5]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 1184970492-chloro-N-(3-cyano-1-phenyl-1H-pyrazol-5-yl)-4-fluoro-5-(3-fluoropyridin-2-yl)benzamide

Product 1

HCID 1184970135-(2-chloro-4-fluoro-5-(3-fluoropyridin-2-yl)benzamido)-1-phenyl-1H-pyrazole-3-carboxamideYield 77.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 2-chloro-N-(3-cyano-1-phenyl-1H-pyrazol-5-yl)-4-fluoro-5-(3-fluoropyridin-2-yl)benzamide (Example 98, 89 mg, 0.20 mmol) in DMSO (5 mL) was added K2CO3 (56 mg, 0.41 mmol) followed by H2O2 (30% aqueous solution, 926 mg, 8.17 mmol). The reaction was stirred at room temperature for 3 hours. The reaction was quenched by the addition of water (20 mL) and extracted into EtOAc (2×20 mL). The combined organic layers were washed with water (2×40 mL), brine (40 mL), dried over magnesium sulphate and concentrated in vacuo. The residue was purified using reverse phase column chromatography eluting from 5-45% MeCN (with 0.1% HCO2H) in water (with 0.1% HCO2H) to afford the title compound as a white solid (70 mg, 75%).

Workup

  1. customThe reaction was quenched by the addition of water (20 mL)
  2. extractionextracted into EtOAc (2×20 mL)
  3. washThe combined organic layers were washed with water (2×40 mL), brine (40 mL)
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified
  7. washeluting from 5-45% MeCN (with 0.1% HCO2H) in water (with 0.1% HCO2H)

Sources & evidence

ORD record
ord-3e6154b20ea2411e9e3788d09501ae41
Source dataset
uspto-grants-2016_05
Patent number
US09328096B2

Reaction notes

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