Hydrogen Peroxide → 4-[(5-Chloro-6-isopropoxypyridin-3-yl)oxy]-3-(2-methoxypyridin-3-yl)benzamide

HRID 1620341Notes

Reaction equation

HRID 1620341 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([O:12][C:13]2[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][C:14]=2[C:21]2[C:22]([O:27][CH3:28])=[N:23][CH:24]=[CH:25][CH:26]=2)[CH:5]=[N:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10].C(=O)([O-])[O-:30].[K+].[K+].OO.O>CS(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([O:12][C:13]2[CH:20]=[CH:19][C:16]([C:17]([NH2:18])=[O:30])=[CH:15][C:14]=2[C:21]2[C:22]([O:27][CH3:28])=[N:23][CH:24]=[CH:25][CH:26]=2)[CH:5]=[N:6][C:7]=1[O:8][CH:9]([CH3:10])[CH3:11]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 11430Potassium CarbonateHCID 666672584-[(5-Chloro-6-isopropoxypyridin-3-yl)oxy]-3-(2-methoxypyridin-3-yl)benzonitrile

Product 1

HCID 666666844-[(5-Chloro-6-isopropoxypyridin-3-yl)oxy]-3-(2-methoxypyridin-3-yl)benzamideYield 85%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 4-[(5-chloro-6-isopropoxypyridin-3-yl)oxy]-3-(2-methoxypyridin-3-yl)benzonitrile (Preparation 26, 534 mg, 1.35 mmol) in DMSO (10.0 mL) was added potassium carbonate (560 mg, 4.05 mmol) and a 30% aqueous solution of hydrogen peroxide (690 μL, 6.74 mmol). The reaction was stirred at room temperature for 1 hour. Water (50 mL) was added to the reaction mixture resulting in the formation of a white precipitate. The precipitate was filtered, washed with water (50 mL) and dried in vacuo to obtain the title compound as a colourless solid (436 mg, 85%), which was used without further purification in the next step.

Workup

  1. customresulting in the formation of a white precipitate
  2. filtrationThe precipitate was filtered
  3. washwashed with water (50 mL)
  4. customdried in vacuo

Sources & evidence

ORD record
ord-606c70c91dd0415087b713df4bcbed94
Source dataset
uspto-grants-2014_07
Patent number
US08772343B2

Reaction notes

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