Hydrogen Peroxide → 4-(5-Chloro-6-cyclopropylpyridin-3-yloxy)-3-(2-methoxypyridin-3-yl)benzamide

HRID 1620353Notes

Reaction equation

HRID 1620353 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([O:11][C:12]2[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][C:13]=2[C:20]2[C:21]([O:26][CH3:27])=[N:22][CH:23]=[CH:24][CH:25]=2)[CH:5]=[N:6][C:7]=1[CH:8]1[CH2:10][CH2:9]1.C(=O)([O-])[O-:29].[K+].[K+].OO.O>CS(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([O:11][C:12]2[CH:19]=[CH:18][C:15]([C:16]([NH2:17])=[O:29])=[CH:14][C:13]=2[C:20]2[C:21]([O:26][CH3:27])=[N:22][CH:23]=[CH:24][CH:25]=2)[CH:5]=[N:6][C:7]=1[CH:8]1[CH2:10][CH2:9]1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 11430Potassium CarbonateHCID 66667121HCID 66667121, compound

Product 1

HCID 666674084-(5-Chloro-6-cyclopropylpyridin-3-yloxy)-3-(2-methoxypyridin-3-yl)benzamideYield 105%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 4-(5-chloro-6-cyclopropylpyridin-3-yloxy)-3-(2-methoxypyridin-3-yl)benzonitrile (Preparation 39, 478 mg, 1.27 mmol) in dimethyl sulfoxide (5 mL) was added potassium carbonate (1.05 g, 7.62 mmol) followed by a 30% aqueous solution of hydrogen peroxide (650 μL, 6.35 mmol). The reaction was stirred 1 hour at room temperature. Water (50 mL) was added and the solution was extracted by ethyl acetate (3×20 mL). The organic layers were combined, dried over magnesium sulfate, filtered and concentrated in vacuo. The crude material was purified by silica gel chromatography eluting with 3% methanol in dichloromethane to afford the title compound as a white solid (528 mg, 87%).

Workup

  1. extractionthe solution was extracted by ethyl acetate (3×20 mL)
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude material was purified by silica gel chromatography
  6. washeluting with 3% methanol in dichloromethane

Sources & evidence

ORD record
ord-0ae2e31eaaa24a11a3ab949eda496712
Source dataset
uspto-grants-2014_07
Patent number
US08772343B2

Reaction notes

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